JPS58116472A - Herbicidal sulfonamide - Google Patents

Abstract

Compounds of the formula <CHEM> wherein A is optionally substituted phenyl, naphthyl, pyridyl, furyl, thienyl, benzyl or phenoxy; W1 is O or S; R20 is H or CH3; X and Y are selected from various organic groups, or X may be Cl; Z is CH or N; and their agriculturally suitable salts, exhibit herbicidal and plant growth regulant effects. The compounds may be formulated for use in conventional manner. They may be made e.g. by reacting an appropriate sulfonyl isocyanate or isothiocyanate of formula ASO2NCW1 with an appropriate aminopyrimidine or aminotriazine.

Description

[Detailed description of the invention]

The present invention relates to herbicidal sulfonamides, particularly selectively
is a pre-emergence herbicide and/or a post-emergence herbicide (dimeth
Regarding (oxymethyl)pyrimidinylsulfonylurea compounds
Ru. U.S. Pat. No. 4,127.405 and U.S. Pat. No. 4,169.
No. 719 is a compound containing -CH, OCH, and a heterosubstituent.
Herbicidal methoxymethylpyrimidine sulfonylurea of the type
A compound is disclosed. European Patent No. 7687 discloses herbicidal sulfoneurea compounds,
Among them, X is CH, or OCR, ZtiCH or N, and yFic, -c, alkyl,
,0CIH,,CN,,C(o)L, 2%C
1f is substituted with 1 to 3 atoms of Br, where
and L is NH,,01(.N(OCHI)CH,,NH(C,-C,"r*ru)
, N(C', -C, alkyl) or cI~c6alkyl
Discloses compounds of which are Coxy. J, Am, Chem, SOC,, R9, Ko072
(1947"), where X is CI, CI (CH, 0, CH, OCH3 or H
And Y is CH(OCHs)! or CH(QCtHs)
T is a compound of and its use as an antibacterial agent.
are doing. The present invention provides a novel compound of formula
A required composition, and general exogenous and/or selective germination
Pre-mortem and/or post-emergent herbicides or seed growth regulators
Regarding. In the formula, X is CHiOCt'1. , CI, C, H, t? c.
HaOC* Hs, 2 is N across CH, and Y is CH! OR, CHtSRl, C)I(OR1),
, OCHs ORt , 0CI((OCHL ) COt
Rs Otake R is H, C (0) R3, Co, R4, C (0
)NR,R・R1 is c, -c, alkyl, R2ke-CI(,CH,-1-C)1(CHs)CH
t-o or -cH, cH; c town-, R1 is C1-mono-alkyl, R4 is c, -, C* alkyl, R5 is H or
keCH, dewa, R- is CI-C, alkyl, Q is O or S, R1 is H% CI C4''7/'kill, C, -C47
/I/Coxy, F, CI, Br%NO,, CFs, C
0tRs, SO*NR1゜R11,80,N(OCR,
)CH,,080,R,,,5(0)1Rts,LCF
,,LCHF*,LCF@CFB Hs C*-C
4 alkenyloxy or C, -C, alkyl (OC'
H, or QC, H. R1 is H, p s C1% B r%CF B s N
Ot 5Ct-C, alkyl or C, -C, alkoxy
and Ro is C, -C, alkyl, CH, CH, O
CR is CH, CH, CI or CH, CH=CH,
R1 and R8 are independently C1-C, alkyl;
Yes, R1ff1 is C, -C, alkyl, CH, CH, OCH
,,CH,C)i,CH,OCR, or C,-C,a
Rukyl (2% substituted with 1 to 3 atoms of C1t or Br)
), and R1, is C1-C, alkyl or C[(, CH=CH
, n is O or 2, L is O, St or SO, R14 is H, CH,,0CHB, F, CI, B
r, No! , SO*NRta Rtt, 08OtRt
t or 5(0)HRts, R11 is H% C1% Br, CHs, up to 0CHs
Or NO. R1 is H%C, -C, alkyl%ClC4alkoxy
, F, CI, Br, CFB, COxRe, SO, N
R. R1,, So, N(OCRs)CH, or 5(
0) nRrs, R8, is H, F, CI, Br% CH, or OC
R. , W is 0 or S, and W is 0 or S, R8, is 8% Cl-4 alkyl, Cl-04 alkoxy
, F % CI, B r s No H, Co, R@,
SO,NR,. R1 SO*N (OCRs) CHst
is 5(0)nRsi, R8, is C1, NO! , CFs , COxRe, So
,N(OCH,)CH,,So,NR,. Rlg, OS
O*Rt*, 5(0)nRisi9 is c, -c,
Alkoxy (substituted with 1 to 5 atoms of CI or F)
) and R16 is Hl or CB; provided that α) the total number of carbon atoms in R1° and R81 is 4 or less
(2) When X is CI-t', 2 is CH and (3
) When W is O, R1, is H% C1% B rs
CH, M9 is CO, R, Ashi, (4) W is O and R1, is H% CI, Br t
(5) When Wl is S, R1゜ is H, R@ (6) Y is oCH, oR, t or 0CH (OCHI) C
O! When R1, 2 is CH. The herbicidal activity is high and/or the synthesis is well tolerated.
For simplicity, preferred compounds are as follows: (1) W, is O, and X is CB, or OCH,
and R3° is H: preferred
Compound (1); R1 is C1-C, alkyl, C, -C, alkoxy, 0
1% No Co, Re, Sow (Ct Cs Al
kill), SOmNRt・R11,5OtN(OCRs)
CJ(s, 080.R1,, CH, 0CIi, or L
CF, H, Ro is CH OCH,,01%080
．． CH, or 80, (C, -C, alkyl),
Fist R1 is CH OCH C1, S O! CH
s or SowN(CHm)t, Ro is CH,, CI, Br, CO, R, or So,
Preferred compounds (2) are CH; Preferred compounds (3) are CH; and particularly preferred
The compound is: 3-(((4-dimethoxy)
dimethyl-6-″methylpyrimidin-2-yl)-ami
Nocarbonylcoaminosulfonyl]-2-thiopheneka
Rubonic acid, methyl ester, 2-chloro-N-[(4-dimethoxymethyl-6-methythyl
Lupyrimidin-2-yl)aminocarbonyl]benzene
Sulfonamide; 2-[:((4-dimethoxymethyl-6-methylpyrimi
din-2-yl)aminocarbonyl]aminosulfonyl
] Benzoic acid, methyl ester; N-((4-dimethoxy
Methyl-6-methylpyrimidin-2-yl)aminocal
[bonyl]-2-methylsulfonylbenzenesulfonamide
N-((4-dimethoxymethyl-6-methylpyrimi
Zin-2-yl)aminocarbonyl)-2-nitrobene
Zenesulfonamide; 2-(((4-dimethoxymethyl-6-methylpyrimidine)
(2-yl)aminocarbonyl-aminosulfonyl)
Benzoic acid, 2-propyl ester; 2-(((4-methyl
-6-(tetrahydropyran-2-yloxymethyl
) pyrimin-2-yl]aminocarbonyl]aminosul
Honyl]benzoic acid, methyl ester; 2-([[4-(hydroxymethyl)-6-methylpyri
midin-2-yl]aminocarbonyl]aminosulfony
] Benzoic acid, methyl ester; 2-(((4-(acetic acid)
methyloxymethyl)-6-methylpyrimidin-2-yl
[aminocarbonyl]aminosulfonyl]benzoic acid,
chill ester. The compound of the synthetic formula I can be prepared by appropriately substituting the formula (■) according to the following reaction formula IK.
The obtained sulfonyl isocyanate is converted into a suitable 2-amino compound.
Produced by reacting K with a heterocyclic compound: (1) (1) Ashi, Y is CJOR-CJSRt, cH(ORt)t or
is CH(QR*Q), and R8 and R2 are as defined above. The reaction of Scheme 1 is carried out using an inert aprotic solvent such as chloride.
2 in methylene, tetrahydrofuran, acetonitrile
It is best performed at temperatures between 0 and 80°C. DABC
O (1,4-diazabicyclo(2,2,2)octane)
A catalytic amount of can be used to accelerate this reaction. If the product is insoluble in the reaction solvent, it can be easily
This can be done by filtration. The product is soluble in the reaction solvent.
When the solvent is evaporated and the residue is dissolved in 1-chlorobutane,
Triturate with a solvent such as methyl ether or methanol,
And then, Jin and Shimashima are killed. The production of incyanate and incyanate 1 is
, U.S. Patent No. 4,127,405, U.S. Patent No. 4169.7
No. 19, European Patent No. 7.687, European Patent No. 1 Turtle No. 480,
Same No. 2 Toshi No. 141, Same No. 2 Kame No. 422, Same No. 30.14
No. 1 and British Patent No. 3065, 116-AK
and the disclosures thereof are incorporated by reference. moreover
, Formula ■1 disclosed in European Patent Publication No. 44212
The sulfonylisocyanate of U.S. Pat. No. 4,127
, 405. (Is) where R8 and R1! is as defined above, in the equation ■
Certain compounds are known. For example, the compound shown below
Product 1'a where X=CH1, CI or 0Ct(,, and R,=CH
5 or C, H, Soc, 69, 3072 (1947) K.
), the disclosure of which is incorporated herein by reference. The triazine of 21b can be prepared by the method outlined in Reaction Schemes 2 and 3.
It can be manufactured in accordance with the law. Reaction formula 2 %Formula% () In the formula, Y = CH(0R1) *or CI(, SR1, R
,=CH, or C, H, and X=R, or OR. The reaction of reaction formula 2a is J, M, McEl va i
n and R,L, C1arke, J, Ame.
r, Chem, Soc,. 69.2657 (1947);
The production of ethyl jetoxyiminoacetate is described in
has been done. The intermediate N-cyanoimidates of formula ■ are
, D. Lwowski, 5ynthesis. 1971, 263, and the cyanamide formula.
(2) in an alcoholic solvent with a suitable compound at 25-80°C.
suitable triazines can be produced by condensation in
can. Alternatively, F, C. 5chaefer and G, A, Peters,
J, Org. Chem, 26, 412 (1961) K-substituted aceto
d) Reaction formula 33 described for IJ sils
Using the reaction, nitriles of formula ■ can be converted to the corresponding iminoes
It can be converted into tels. Is it possible to release?
Alternatively, use amidis as described in the above references.
can be converted to nium hydrochloride. The compound of formula ■ is
The compound 1bK can be converted by the reaction of reaction formula 3C.
, where ■ is mixed with a compound of formula ■ at 0 to 30°C for 3~
suitable in the presence of 4 equivalents of a suitable sodium alkoxide
contact in alcohol. The product evaporates the solvent and
It can be isolated by neutralization with aqueous acetic acid and heating.
can. Reaction formula 3 () () (3) ([) In the formula, YaCH(ORI) CH,SR,,CH,0THP
or CH(ORvO), R1 is CFIs or Ct Hs, and X is R
It is one-straddle SCH. Compounds of formula 1c can be prepared according to the reaction sequence outlined in Scheme 4.
can be manufactured by Reaction formula 4 In the formula, Y is CH(ORI)! , cti(QRtQ), CH,
S.R. or CH,0THP and R1 and R3 are as defined above. The reactions of equations 4a and 4b are W, 13raker
. et ml, 16c, cit,
Implement as described below. U) Reactions of reaction formulas 5maro and 5b are 2-amino-4-hydro
Description of roxy-6-simethoxymethylpyrimidine
Performed as described (J. Is D@Graw and V, H, Brown, J.
, Het. Chem,, 13. 439 (1976) )o
The silver salt of XI is made by combining ammonia with XI and an equivalent amount of silver nitrate.
It can be produced by adding it to an aqueous solution of Dried nine silver salt and add 1 portion of methyl iodide or ethyl iodide.
in a non-polar solvent such as benzene at 25-80°C.
Column chromatography or recrystallization
to produce pyrimidines of formula 1d after purification by
I can do it. Alternatively, compounds of formula 1d can be prepared using the corresponding chloropyrimin
It can be produced through gins (We). these are
can be obtained by the reaction of reaction formula 6a, where formula
Compound I with 2 to 5 phosphorus oxychloride and 20 to 40
React for 3 to 30 hours at ℃. The product is an excess of P
OC1, was removed in vacuo, the residue was treated with ice water, and the organic solution
Extract in medium, concentrate, crystallize or column chromatograph
It is isolated by roughy treatment. Then Chloro
pyrimidines with 1 equivalent of the appropriate sodium alkoxy
in alcohol at 0 to 30°C, and then
When concentrated with
It can be converted into a compound. Reaction formula 6 (6a) N Hibiki (6b) (1- (1 (1) In the formula, Y is CH (ORs) t, CH, SR1 or 0H (
QR嘗Q) is, R8゜ is H or CH, and R3 is CH, or
dc, H,. Cyclic acetals of formula 1e can be reacted from compounds of formula 1a.
It can be produced by acetal exchange according to Equation 7.
. (la) (XV) (We) In the formula, X%Q%2%R1 and R,,I: is defined as 9 and O.
be. The reaction of Reaction Scheme 7 is performed by combining an acyclic acetal in an inert solvent.
1 equivalent of a compound of formula Xv and slightly more than 1 equivalent
Acidic catalysts, such as p-toluenesulfonic acid or triphenyl
Heating in the presence of boron fluoride etherate and simultaneously producing by-products
It is carried out by distilling something. 2He compound
is isolated by extraction with an organic solvent and then crystallized or oxidized.
Can be purified by ram chromatography
. The synthesis of the formula 1.9ON-methyl compound is shown in Reaction Scheme 8.
This can be achieved by following steps. Reaction formula 8 (Seal f) (XV
I) In the formula, X is Rlt or OR, Y is CH(ORs)*, CH(Q, RIQ), CHI
OR. Also, CH, SR, and R8 and Q are as defined above. The reaction of reaction formula 8m is Ib and 1 equivalent of sodium hydride
and dimethyl carbonate, respectively.
Solvents such as tetrahydrofuran or dimethylform
This can be done by stirring in amide for 1 to 3 days.
Ru. The product of formula X is obtained by evaporating the solvent and neutralizing with aqueous acetic acid.
and the product can be isolated by passing it through.
Wear. In the reaction of reaction formula 8b, xvI is reacted with tetrahydride at 0-30°C
Added to a slurry of 1 equivalent of sodium hydride in Lofuran
Stir for 0.5 hours, add methyl iodide, and add 1-2 hours.
Heat at reflux for 0 hours, then combine with water and aqueous sodium hydroxide.
Stir at 20-30℃ for 1-20 hours.
Implemented by K. The product is obtained by evaporating the solvent, adding ice water, and heating.
Isolate it. Compounds of formulas 1h and li can be prepared by the reaction of formula 9.
can be manufactured by This reaction is expressed by equation 5c and
Performed similarly to the procedure described for reaction 5d.
. Reaction formula 9 % formula %) () () (9C) (Ii) In the formula, X, R, R8 and R2° are as defined above.
It is shi. The compound of formula Ib is a compound of formula ■1 according to reaction formula 10.
It can be produced by acidic hydrolysis of substances. (IR) (Ib) where A, X1R1e and 2 are as defined above. The reaction of Equation 10 is carried out using a catalytic amount of a strong acid, such as hydrochloric acid or
is a solution of la in aqueous acetone containing sulfuric acid or S
Stir the suspension at 0-30°C, then concentrate and
This is done by treating the product in a furnace. Compound No. 1b is then converted into formulas lc and Id according to Reaction Scheme 11.
It depends on whether it is converted to a compound of t or le. Reaction formula 11 (1) () () In the formula, A, Xs Z%Rs -R4, Rw, R@ and R
1° is as defined above. The reaction of reaction formula 11 is carried out using at least one equivalent of the compound No. 1b.
Alkyl carboxylic acid anhydride, carbonyl chloride, chloride
In an inert solvent with carbamoyl
Excess acid acceptors such as pyridine, triethylamine,
or in the presence of aqueous sodium carbonate and then
Acidification and crystallization of the product or extraction into an organic solvent
Isolation is carried out by K. Or %R
. The compound 21e of =H is one equivalent of the appropriate compound 21b.
Contact with an appropriate amount of alkyl isocyanate in an inert solvent.
It can be produced by touching the product and treating the product in a furnace.
can. A compound of formula (■) is produced by the reaction of reaction formula 12.
You can also do that. (XVIJ (MX) (12b) where R1., X and person are as defined above, but
Dashi R1, hat 1, R1, and R1, are CO, R,
do not have. The reaction of reaction formula 1211 is the same as that described for reaction formula 1.
Carry out in the same way. The resulting compound of formula x■, 3
~5 equivalents of diisobutylaluminum hydride and ether
By contacting at -20-20C in a solvent, K.
can be converted into a compound of formula Ib, and then the reaction mixture
is quenched with aqueous mineral acid and extracted with an organic solvent. Dissolve the product
It can be isolated by evaporation of the medium and crystallization. Scheme 13 schematically depicts a compound of formula X■. Reaction Formula 13 (13) % Formula %() ) ) (13) ) where R8 and R3° are as defined above. The pyrimidine of formula XX is Z, Budisinsky
andF, Houbrnek, Col 1. Cme
ch, Chem, Comm,. 26.2871 (1961) VC. this
is heated to 80-140℃ in an autoclave with ammonia or
is heated with methylamine to form an amino acid of formula XXI.
can generate classes. These are measured using conventional methods.
can be esterified with alcohol and acid, then solvent
is evaporated, neutralized and heated to produce a compound of formula Xvla.
to be accomplished. The production of XVll b (Rto = H) is G, Da
vies, eta+1. ,J,Org,Chem,.
26,2755 It was reported in the media, and N-Methi
compound (Rt.=CH,) is prepared in a similar manner.
be able to. The reaction of Reaction Equation 12b is written in the same way as Reaction Equation 6b.
Follow the steps below. Example 1 12(
6.9 g of sodium pellets in 1 g of toluene) K,
20Ii of acetone was added dropwise at 0-20°C. child
The mixture was stirred overnight at room temperature, concentrated under reduced pressure, and the product was
Precipitate with ether and heat. 1011j in ice water
Acetic acid was added and the β-diketone was extracted with methylene chloride. The residue from the concentration of the organic solvent was transferred to a 25J7 Guajinka.
Heat to 80-90℃ for 30 minutes in a pot and cool.
, aged in methylene chloride, oven-heated and dried over sodium sulfate.
Dry, treat with P, concentrate under reduced pressure, grind with petroleum ether,
11 g of 2-amino-4-dimethoxymethyl-6-methy
Lupyrimidine, m, 9.69-71°C (Literature, m, p
, 71-74°C). NMR (CDCl m ) δ: L3 (s, 3), 3.3
(@. 6), &O(s, 1), 5.9(br s, 2), 6
．． 7(8,1). Example 2 0.39 2-amino-4-dimethane in 50-ether
Solution of toxymethyl-6-methylpyrimidine, 0.
469 o-chloropenvinsulfonyl incyane
Stir overnight at room temperature. The product was filtered and washed with hexane to 0.5.9 N
MR (CDCI 8 ) δ: L5 (s, 3), 3.4 (
s, 6), 5.2 (s, 1), 7.1 (s, 1), 7.
4 (m, 3), 7.9 (br 5ki), 8.3 (m
, l). Example 3 309 Methylgyl IJ Co in 10011j Toluene
rate, 33Ii of dihydropyran, and 0.2.9
of p-toluenesulfonic acid was stirred overnight at room temperature.
Zeru. After cooling to -5°C, sodium chloride of 6.811
24°C at -5°C to 8°C.
Added seton. Stirring was continued for 20 hours at room temperature, then
Hexane was added and the solution was poured into ice water and distributed.
. The aqueous phase was extracted with ether and acidified with 20-acetic acid;
The organic phase was dried (Mg5O4) and concentrated, leaving a residue of 80%
with 28II guanidine carbonate at ~90°C
Heated for 1 hour. When ice water is added to a cold reaction mixture,
The product precipitates and is filtered and dried to give the title compound.
A substance, m, p, 109-100.5°C was obtained. NMR (CDC1m) δ: 1.7 (brs, 6), z
3 ("s3)% 3.6 (br m, 2),
4.5 (d, 2), 4.7 (m, 1), 5.4 (brs
, 2), 6.6 (brs. 1). Example 4 Product from Example 3 in ether of 59m&25I
3.75 g of 2-methoxycarbonylbenze in a solution of
sulfonyl isocyanate, and the mixture was
Stir in a nitrogen atmosphere for an hour. The precipitated product was heated in a furnace and washed with ether.
The title compound of f, m, 9.126-128°C (decomposed)
Obtained. Example 5 Product prepared in Example 4 in 59 m acetone
61i solution with 3 m IN aqueous HCI for 3 days on VC.
Stir at room temperature for a while, concentrate under reduced pressure, and dilute the residue with water.
After thorough washing, the title compound of 4Ii, m, p, 14Q~
A temperature of 141°C was obtained. NMR (CDC13+DMSOds) δ: 15
(” t3), 3.9 (S, 3), 4.6 (brs, 2
), 7.0 (brS, 1), 7.6 (m, 3), 8.3
(m, 1), 9.6 (brS, 1). Example 6 0.511 of the compound from Example 5 was added with 1-acetic anhydride.
and 1d pyrimidine were added. 145-1 at room temperature
50°C was obtained. N M R (CDCl m ) δ42 (S, 3),'z
, 6(''*3)% 3.9 (s, 3), 5
．． 2 (S, 2), 6.9 (1, 1), 7.7 (m, 3)
, 8.3 (brs, 1), 8.4 (m, 1),
1 & 1 (brs, 1). Table 1a ”7 R8R20X X 7el
HII CH2O)1(OCH3)21
50-153CO2CH,HHCH3OM(OCH3)
2121-125So, CH, HHCH, cH (oco
)2152-155No2HHCH3,CH(OCR
,)21J+4-152Co,,CH(CB3)2HI
4 CH3OH(OCH3)273-79Co,,C
2H3HHC13CM (OCH3C13C, HHC13
C1l(OCH3)2sr HHCH,C
H(OCH3)2CH3HHCH3Cl(OCII,)
2C2H, HH0830M (OCR,)2802-n-
C, H, Hu, CH, CH (OCR,)2135
-145 (decomposition) E02N (CH3)2HHCH2Cl
, CH(OCH3)2146-1570CH3HHC
H3Cl1(OCII3)2CO2CH2CH=CH2
11HCH3C1(OCH,)2GCF2CF,,HH
HOH, CM (OCH3) 2yu 88 Information
xy li” IC120CH3HHCH2Cl,
CH(OCH3)20802CMCI2)I HC
H,CB(OCH3)2sc21(,HHCH2Cl,
Cl4(OCH3)20502CB, HI
iC)i3CH(OCTl,)20502Cii,
HHCH3Cl(OCH3)2cO2CH,
(X, CCH, HII CH3Cl(OCH3)2s
o2c214. HIt CH3ch (oc
H, ),. No25-CF3HC12C)L3cCl2C)L3゜
K) 2-54<, B73<l HCH, CI(OCR
,)2QC,H,5-No2H0H3CH(OCH,)
2So2N(CM,)C2H56-No2HC13C)
l(hemp 3)2C15<l HCH,CH(OCH3)
. 802CH,5Mcl HCH3Cl(OCH3)2
CO2C134-F HCH3OH(OCII,)2
0CH2CH<H2HHCH3Cl(OCR,)2CH
(times,)CB, HHCH3Cl(OCii,)2
So2CF, H1(CH,CH(OCI(,
)2 F2HHCH,CM(CCH3)2 0CR2CH<HCII, HHCH,CM(OC
R, )2C1, HCH, CH3Cl (mouth 5)2 GO2CO, HCH3Cl, CB((XJI,)2
R7R8 Jou Su Y
! -” Self-nee S Nishini and Go2CH2CH, HC
113, CB, CH (OCH3) 2 bacteria 2CH3HC
II3CH3CH(Oc)r3)2S02N(0M3)
2HGO, CH3Cl (OCH, ),. CH(CH3)2HCH3Cl13C)I(OCH3)
20CH3,HCH3CB5C1(OCH3)2SCH
,HCH3OM, CH(OCH3)2So2-n-
C,H7HCH3Cl, Ch(OCH,)2B-C
4H,HCH2O:', CM(OCR,)2Q-B
-CbH9HCH3CH3OM(OCH,)2NO2H
CI3CBCl5CB3C! 3) 2Co2-A-C4H
9HCH3OH3C1i (OCH3)2 Table 1b 5 R7R8 InformationX! ! , J! 2) No2HHC
H, C120THP IF9-132Br
HHC1'l, CH20THPCI
HHC13C120T)IF 148-150S
02CH3HHCC13C,0THr' 161-
165F HHCH3CH2°荀PHHH
CH3CH2°TIP Go2CH,HH0H3CH20THP 126-'
128CH3HHCH3CH20'IHP,! 1i02N(CH,)2h HCH3CH2Q
'ff1PsO2-B-C, H2N II CH
,CH20THPOCII, HHCH2C
l, °H20'lp flame-C, H7H11CH, C) I2
．． ”TIPCH20CR3HII CH2Cl,
CM20THPCo2C12CM-CH2H)I
CB5C120THPR7) 18”20A Y
rS02N(0M3)2HCB5CH3CH2Ku
PQC2H5HCH3Cl13 °H2°'L5P
Go2Et HCH3Cl3C120'I!
H1'0CF2CF2HH0H3°H3°B2°Ti1
PCH20CH, HCH2CH2O) 120TIPCI
HCH3CH3CH20THPSC2
H, HCH3Cl, C11120THP802C
O2CIl=CH2HH0M30M20Ti(PSCF
, HHC13°H20 dish CH (my 3)C
H3HHCM3C)+20THP table 10"R8)120X!% plate
CI HHC1l, CH20H13
l30-132Co2C' HHCH3Cl120H
141so2am, Hu C
H,0M20H255 (disassembly)? IQ2HHCH,0H
20H11;'-116co2cn(cm3)2HH0
M3CH20H154-Takumi7002C2H5HIICH
3CH20HCF3HHCH2Cl, CH20H Br HHCH3CH3CH20HCH
CH, °H2°11 OCR3H)I CI, °H20HcO2CH
2CH'clI2HHCH3CH20HOC72CF2
HH11C13C120T (h R8R20X
Y Kanayu CH20CR, HHC03 (, B2
0HOs02CHCI2HHCH30M2°H80♂,
HHCH3°H2°H0802CH,HH
CM, CH20H0802C,H,HH0M3
°H2OHCO2CH2CH2hemp, HHCH
3Cl(2硼5O2C2I'l5HHCH2CH3CH
20HNo25<F, )I CH, CH20KS0
2-3-C,H73-CI RC113Cki20H
CX, B55-No2HCH, CI, 0H5o2N (
OB,)C2H,6-No2HCH3Cl120HC1
)CI HCH3°H2°H 8o2CM, )CI H0M2CH30
H20HCo2CH, 4-F HCH, CH20HN
o2HCH3CM3CH2OH Br H-0M3CI, CH20
H(J HCH3CH3CH, (XiS
o2CH, HCH3CH3CH20HF
HC113CM30C113CHC1 (, CH30H
20H Co2CH3HCH3CH3CII20HR7”8
R20X Y Fuji-CH, HCl, °H3
°) +26H 802-1<, H7HCH30830M2°HSCF,
HC130H, CH20H5o2CH2C
M<H2HCH3Ck13CH20H8CH2CH3H
CH, °H3°H2°HoCH2CH″cH2HCH3
CH3CI(20HOCR2CCCH3”)<H2HC
H3CH3CH20HOH2QEt HCH
3Cl3CH2°HOH(OCR3)CH,HCH3C
l3CH2°HCO2CH2CH2C1)ICH3CH
3CH20H〇-ball<5H7HCI3°H3CH20H
1-C411,HCH3°H3C1120H50,Et
li HCH, CH20H tri-C4H
9HHCH3CH20B O-A-C4H9HHCH,CH20H Kabuto-04H,H
HCH3°H20H K)2NCCM,>C2II, HHCH3,C1
120H table 1d 〉 R? R8k20X Y a
, 1 ward 11 HHCH3Cl (OCR20H
20) HHB 0M301(OEt)2 HHHC7,Ck120cOc11゜HHHC113CH2SCH3 H1(H0M3CEI(ocH2CH2CH20)(:
l HHCH3Cl (OCR2CH20)
158-163C1l(an3c)13C)I(times
jICH20) CI HJ C2H,ell
(OCR2C120) CI It HC5C
H(OCH2CH2CH20)C16PCIHCH3C
H(OCH2CH2CH2o)CL It
CR3CH3α (prison H2CH?2θ) C14-F H
CH3Cl(It)2C1 HCH2O)[(O
lt)20H3HII CH3°H(OMt)20H
3H)l C2)I, CB(Onut)2x7”
s'x=X Song C'H311HCH3CH25CH. 02H,H)I CH3Cl120COcK43C,
,H,HC1C13C°H2OCOCH3002CH3
HCH3Cl (SCH2cB2cR2g) ■ Co2>, HHC, H5CH (OE, t) 280
20H3HHCH3CH20COEtBO2CH33'
″F HCM, CR25CIi3R,, Rs Information
XY Colorimetric 5o2CH, HHCH, CH (OCR2CH20)
193-195 (decomposition) S02CH36CH,CH,ell (OCR2C120
)S02CH36-o-! ! -C3H7 HCH,C)IC times 2CH20) S02CH36-1-C3H7,H(13CB(OCR
2CM20)002N(CH3)2H11CH3Cl2
0CO-n-C3H7802N(C13)2HHCl,
CH2 True 502N (Q(,)2HHC1130H
(SCH(CI!3)C1l,5)SO3M(CH3)
2HH(m3QH(OCH2CH20) 185-1
87so,z+(CH3)2II CH3Cl,
CM(OCR20H20)SO3M(C13)26-
NO2II 0M3CH (OCR, CH20) No2
3-Br H0M3CI (OCR2CH20) No2
6-CI Cl5CH3CH (QC) 12CI+20
)No2HHC2H3CH(OCfi,,CH20)N
OL, u rr C) I3
a1((ocH2C120) 179?:,)N
o23-F! (CH30H(OCR2CI2G)C
O2CH2cH=CH2HHcH3CH(OCH2CH
20) Co2CH2CH, -CH3I, HCH,
CH(OCR2CH2CH20)Br HHC
H3CH (JCH2C■2S)Br HI
Cl, CH3Cl20BO-h R8 小XY
m, 1 box Br HC1l,
CH, C120CONHCH3CF, HHC
i13 α(L)C)12C1i20)CF,
HHCH3Cl125j, ;tgo-(Et)2I
I HCH3OH (times, ■, 0) OCH2cH3
HC2H501(OCM2CH20)O-! 1-c4x
9HHCH, CH (OCR20H20) SH-C, R7
HHCH3OH (times 2CH20)0-C1l, CFiw
CH2HHQ(,CM(OCH,(m20)802CF
3'B, CH, CH (OCR20H20)802C
F, 5-CF5)I CH30H(OEt)
25020F, HCH,CH(OEt)
25o2-A-C, H3P HCH3OH(oa
t)280,-! 1-C3H7HCH3OH3C)I(
OEt)2!1102-B-C3117HHC113°
1ll (0°H2°H20) 14k (min.
Ino0CF2C72Hil I (cH30H20
G.O.C.I. 0CF2CF21f K 11 C2H,
CH20COCH30c! 2CF,,HIIH
Cl, , OH,0COCH. 0802C2H,HH0M3 °H20coCH3Q
120Et 6-F HCM, 0H20
COQI. CH2 town, 0H2CI HII CH3OH (OC
R(CB3)CH20)R7R8R20X y
5i! 802N(Cl,)Et H11CH
3OH,0CO7tSo2N(CB,)It H)I
CI3GM20COCl5G, )2So2N(CH
,)Et HHC113Cl(OCR2CH20H2
0) Table 10 Cheer beak CM, HHQ'C) 130H (CCJ(,)
2OCR,HH0CH3co(or:u,)20CF2
CF2HHHOCH3C8 (OCM, ). '7 R8R20X Y Shim I
CH2ocH,II)I 001120M,
CM (OCR,). :1SO2CHC12H110CH3C11 (OCR,
)2ec2H,II CH,OCR,C1(OCR
,)20802cH,II HOCR,CH(OC
R,)20802C,H,HHOCH,CH(OCII
, )2Co2C112cH20CII, HHOCR
,C11(OCR,)2So2C2H,HHOCR,C
H(OCH3)2K125-CF, H0CR30H(
OCH3)2802-! 1-C,H73-CI H-
0CII, CB(OCR,)2DC2H,)No2
If 0CR20R,CH(OCH,)2So2N(
0M3) C2H,6-No211 0CH3C8(OC
H,)2::l, 5-cl H0CR3
CH(OCH3)2Co, CB55<L HOCR
, CH(OCH3)2', 020M, 4-)
'H times 56H (OCR,) 2 table 1f 5 R? R8R20X Y Beast Mu!
No2) i M 001130m20'151P
Br HHOCH3CH20WPCI
HH scream 3 Silk 20'l! P802°R,1
i H night 3 °H2°Tl4PF
11 III OCR, Cl2O'ff1P1
1 HI CcH,'a2ospco
2°H3HHoCH3cH20°mpc113HHOc
I(3CH20THP802N(CM,)2HH001
30M20fI51P″2-!?;3H7HH0CB3
an2osp■H5HH times, an2o'mp DB-C3H7HCH, OCR, CH20TIIPC
120CR, HCM, OCR, °H20'1EPGo
2CI2C1l<H2N 11 0CH, CM2O
'1MPC1G-CI HOCR,el12UfiP
Table 1g R7R81'20X! Self! + ++k □- CI Hit 0CR3C112°1(
co2°11. HHOCH, C1i, (II
So2C1(,11II OCH,0M2aH17
0 (decomposition) No2HM OCH, CM20M GO20H (CH3) 211 RCcH, 0M20
HCo2C,)i, HH(XljH,CH2
011CF3EHOCH3CH2oH Br HHOCR,CH20HOCR,H
Cm, 0CR30H2aR C2)15 ■ H,,OCH,CH20
HK;027-C, H2N HOCH, °lI20
BsO2N(C13)2HH0C11,CH20HOC
R,HHOCR,C120H Co2CII2C1l-Ci12HH0Ck12CH3
CH20ftOCF'2CF2HII HOCR,
0M20H"? RsR2oxH4 CH20C11, HH00130M20H0802CI
iC1,II H0CH3Cfi20i15C,H
,HCH30CH30H,0ROFpO2CH,II
H0CFI, (:11. C120110802C
211,11HOCR3C1i2oHGo2CM2CM
20CR, 11H0CII, CH20HK)2G2
11. HHOCR,CE20My)25-CF
, K OCHs CH20M5°2□3H73zu
lit Island 30 剪 Oc, H,) No 2 HOCR,
CH,0HK)2NCCB,,')C2II, 6-
No2II OCI, C ■2 Rin C1) C1ml
times) 0H2 country K) 2CB, 5-CI HOCR30H2
CICo2Cm134-F HOCH3CM20H table
1h 17'R8 vox! L day)HHH0CR
30H (OCR2C120) H1 (HOC113CII
I(It)2HHH0C2II, CB, 0CDCJI. II H1(OCR, CI, 8CH. II HROCR3(m(times,, CI2CM2
Cl2CHHαm, CM(αm2cu2) capture
Chaos 2 (decomposition) cl HCH30CR, ■ (possible 2
CH20) CI It HQC2II,
OH(OCR20M20)CIH')I OCR,C
H (■H2CB, C120) 186-1 title C16-
CI H00M30CR (OCR2CR2CH20)
CI HC130CH, (1((OCII20
H2CM20)C1k-1HOCH30H(QEt)2
CI HH times 3α(or;t)2143-11
)5CH3HH0CH3CH(OEt)2 CB3HHQC21f, CH(0:t)2R?
R81X 7 0CR3)I H0CH3CH(OEt)2So2
CI, 3-F H0CH3CH2SCI(3
R7R8R20X Y 7so2cn3
HOCH3cH(ocH2an2o) 182-18
9 (decomposition) l 502CH3cH30CH3CH (OcH2420)5
02CH36-O-…-C3117H0CH3Cfl(
OCR20H20)+502CH33-Knee〇, H7H
0CR3C)l(OCH2C120)so2tt(cn
3) 2HH0CR3CI+20CO7B-C,H7So
2N(CH3)21(HOC1+3CH(Ok;t)2
138-141S02N(CH3)2HCH30CH3
C) I(ocH2CH20)so2n(ah3)26-
No2H0CH3CH (OCR20H20) No2)!
3r HQC113CH (OCH2CM20) No.
26-CI CM, OCR, CH (OCR20H2
0)+1o2u Hoc2)I5cH(oca2
co2o) No2HH0CH3CH (OCR2CH20
)rJo23-F HOCH,CH(OCH2CH
2Q) co2CIi2cH<n2u HOCH,
cn (oCa2cH2o) CO2CH2CH music 2 HH
0CR3CH(■H2CH20H20)Br
HH0CR3c]I(sea2an2s)Br
11 H0CH3CH20Co20H3Er
11 0H3°CM30 to 12°(A
)Nk4CH. R? R8R20XY rCF,
HH0CR3CH(CCH2CH21))C
F, HHOCR3CM, St':tso2N
CIri2 Hn oca3 CH(OCH
2Co20)OCR2CH,ill QC,H,01
(OCR20H2Q)0-n-C411,HHOCH3
CH(OCH2CM,,0)o-i-c3a7HHL)
CH3an(ocu2co2o)o-ah2ca==c
n2HHOCH,CH(OCH2CM20)802CF
, H0CH3CHCOCH2CH20>
5o2CF, m, -cy3HOCH,ah(ob
t)2So2CF3H0CR3CH(OEt)25o2
-A-C;3H71(110CH,0H((Et)2S
o2-B-C3H7, HCH30CH, an(OF, t
)2So2-n-C3H7HHocu3CH(OCH2
CH20)CX22CF,)l HH0CR3,0
H20COCH30CF2CF2HHHQC2H5CH
20COCH300F20F, J HH0CH3C
H20CO°H3O5O2C2II, H,HOC
H,CH,,0COCH. Cl2Qk;t6-F HOCH,CI!
20COCR3CI2CH2c112CI HH0C
H3CH(Fx; II(CH3)CH2O) $02N(
C13) Et Hll (X; H3': II20C
O)t502N(0M3)Et 11 H0C
R30H2uGON(C13)2R? R8R20XY
a So, N(C;H,)FJt H110CR3CM(
OCR2C112CH20)Co2CH,ROCH,C
F, CC, CH2CT12CH20') 150-1
535o2N (Cl,)2 ■ H0CH
30H (OCTI2CI42CH20) 130 (minutes
Solution) Table 11 CI HHCI CH (OCH3),,
164-166Bf HHCL C
H(OCH3)2CH3HHc1cH(OCH3)2 C2H,HHC1ca(ccrt3)2CCH3HCH
,CI CH(OCli3)20CF20F,HH
II CI CH (OCR,)2R7R8R20
X X Mu West) CH2″H, HHCI c
I((Scream 3)2oS02CHC12HHCICH(OC
H3) 2!3C2H5HHCI CH (OCH3)
20802CH, HHCI CH (OCH3) 20
s02C2H, HHCI CH(OCH3)2co
2Cn2co2ocH3HHCI CH(QC)+
3) 2So2C2H, HHCI CH (OCH3)
2No25-CF HCI CH(OCH3)2
) SO2-A<;H,3-C1HCI CH(OCH
,)2″♂55-No,, ° CI CM (screaming pregnant)
2So, N(Ci13)C, R56-No2HCI
CM(OCH3)2(:l 5-CI
HCI CH (OCH3) 2802° H3 CI
HCI CM(OCH3)2Co2(H3b-
y HCI CH (OCH3)2 Table 1j R7R8R? OX
HHCH3Cl(OCH3)2Co2GM3HHC
H3°H(H3)2113-120So2CH,HHC
120H3Cl(OCH3)2No2HHCH36H(
OCli3)2C02C1f(0M3)2)IHCH3
CH(OCH3)2Co2G,H,)[)ICE,
CH(OCH3)2CF, HH0M
3 °H(OCH3)2Br HHC
H2Cl, cH(acn3)2CI(OK,)2i
1 M CI43CM (OCCl43C,,H,
Hu CH3cH(oc++3)2S021i, 17
M 11 CH30H (mouth 3) 2802N (0M
3) 2B 11 0H3CB(OCH3)2OCR
2CB<HCl13HHC1i, CH(OCli
, )2Go2C12CM<H2HCM30H30H(O
CR,)2R,Ft8 Deception X Y J)O
CF2CF2if HHCl, CM(OC
R,)2C120CR,B HCH2Cl3ch(
oc5)2QSO2CHCI2HHCH3Cl(OCR
,)25C2H5HHCH3Cl(OCH3)2050
20H3HII C1(36H(OCH3)2O80
2C2H,)I HC83CM(OCH5)
2Co2CH2CH20CR, HHCM, cn(
oca3)2so2°f, HHC1
(, C11(OCH3)2NO25<F, HC13C
H(OCH3)2So2"rA-C3H73-CI
HCH3Cl(OCH3)2CC,R55-No2HC
H,CM(OCH3)2So2N(CB,)C2H,6
-No2HCH,CH(OCH3)2C1)CI H
Cl5CH(OCH3),. 5020B35-CI H0M3CH(OCH3)2
co2cE, 4-F HCH30M (OC
H3) 2 Table 1 5 R7R8R20X X m, B, 2) --□- No2HHCH3CH20'114P Br HHCH3CH2:rTHPCI
HHCH3CH20THPF'H
HCH30M20r) iP502CH3HCH3CH3
CH20THPHHHCCH3CH20TH PCo2C,HH0M5CH20THP(m,
HHCM3C120THPSo2N(CH,)2H
HCH3CM2O'I'HP802-H-C3117u
HCH3°H2°1POcH3HHcII2CH
3CH2oTHP04-C3H7HHCH3Cl,,0
THPOH20CH3HHC113CH2Q'n1Pc
O2CH2CH-CH2HHcH3cH2o'rHP table
16 R7R8R20X X d CI HHC)I, CH20I! 0
026H3HCH30H, CI2°H802°kl,
HHCH30H, 0HNo2. H
HCH3CH20HCo2CH(C'H5)2HHCH
3CH20HcO2C2H5HHCH2CH3CE20
HCF, HHCH3CH2°HBr
HH(B, CH2°!(CH,HHC
H3°H2GI C2H5HEI C) 100M20H8o2B-C,
H2OH0M30H20H8o2N(Cl,)2HHC
1f3CH20HOCH,II)I C113
CH2 circleCo2CH2CH<H2OCH3CH3CH2
aHOCT2CFI HHCH, CM2C1l
iR7R8R20X X m,)4self! ---
■■１－－■■Lea■■－１－－CM20CM311
HCH, CI, 0H0802CHCI2HHCH
,CH20H5C2R,HII CH3Cl1,0R
O802cH3HHCH2CH3CH20H0802C
,H,,HHCH3CH20HCo2c1t2cH2o
cH3H11CM, C) It20H5o2C2H
, Hl(C13°H20HNo25-CF3HC130
H20H 8021″-C3H73-CI HC13C13CH
20HOc2″″N02HcH3CH20H5o, N(
CH3)C21I, 6-No2HCM, CH
20HC1Hl Ha Cm! , CH2α1502
(m, 5-CI HCH, CH20HCo
2CH,' 4-F HCH30M20r table 1m R7”8 R20X X dNo2HHC
H3Cl1(QC2H,)2No2HCH,CH,°H
20 cocH3No2HHCl, °H2BCH. Br Fi HCH3CH20GOt
fHCH3Cl HHCH3°H2oCO
2°H3F HHC13CH2sC2N!
. F II HCl, CH(OC
H2CH20)S02CH3HIICH2CH3CB2
0Coc2H5SO2CH3HHCB3CH(ocH(
CH3) CH20) 8020H311HC13G) 1(
OCH2CM2C)C13G)1(OCH2CHC13
°H2s0H2°H3HHHC13C120COCR. Co2Cl, HHC)I, C120C
ON(C1i3)2Co2CH,HHC1130u(Q
C) 120M20) Co2Cl, HC13°
H3CM20COCH3”7 F’8 R
20K X dC02°H3HHC1! ,
°H2SC,I(. CM, HHCH2Cl, CH(QC,
H,)20H,HHCl, 0H20CO2C2H
. 502N(CH3)2HHCH3CH2oCON(C2
H5)2sO2N(CM,)211 HCH,C1
120GO-1-C3H7″2″″!!-C,H,HI
ICE, °H2"Naki1-0♂71502-B
-C,L, HHCH,C1(QC,H,)20
cII3HHCH3CH (SCH2CH2S) times 3HH
CH3Ck12SCH3 0-B-C3H7HHCM, CH20CO2Cl
. Flame 7-C3H7HHCH3CH2Cf, oN (C2H5
)2CM20CR3HHCH3CH20COCH. CH2CH211H0M3 °H20c02CH3
Co2C12CH<H2HHCH,CH(QC2H5)
2 Table 1n R7R8 Information
7-121co2CH,HH0CH3C)1(OCR,
)2135-158So2CH,HH0CH3CH(O
CH,)2No2HH0CR3CI(sound3)2 co2cn(cH,)2m HOCR,CI(OC
M,)2C02C2H5HH0CH3C1((QC)I
, )2CF, HH0CH2CH, an(o
cH3)2By-HH0CH3CH(OCR,)2CB
3HHOCH30M (OCR,) 2 yen, H
H0CR3CI((X';H,)2sO2-2-C31
17H”H0CH3CH(OCH3)2s02N(
OH3)2HII 0CI3CI! (OCH,)2O
CR3HH0CR2CB, CB(OCII,)2Co
2C112CH=CH2HCH30CR3Cl(OCH
,)2ccr2ay,,H* H0CH3co(c
cn,)2”7 Ra 1”20X
X Yoji Q) CI! 2oCH3HHoC)I3C
H(oc113)20802CHCI2HHOCH,(
Jl(OCR,)2SC,H,HHOCH3CH(OC
H3) 20802CM, HII OCH,
CH((CH,)20802C2B, HH0C
R30H (0°H3)2Co2CH2CB20CI3H
H0CH30H((IcH,)2So2C2H, HH0
CH3CH(OCH,)2No25-CF, H0CR
3 H(OCR,)2sO2-r4-C, k173-C
I HOCH,CH(OCH,)2QC2H,5-N
o2II 0CH3CI ((XJI3). 5o2h(cH3)C'2H56-rio2Hcca,
cH(ocH,)2C15-CI H0CR3C
l(QCli,)2s02cn3)CIHCICH,c
H(Cc,3)2Co2cH,4-F HOCR,C
H(LCH3)2f-,10"? R8"20X K mN0
2H,M 00830M20'ff1PBr
HH0CII, CH20THPCI
HHOCH, CH20T) fP 136-1
39J02°H,)I H0CR30H20THP
F HH0CR3CH20THPHHHHO
CH, CH20THP Co2Ckl, HHOCH, cIi20TH
PCB3H1! OCH, 0H20 resistance P150271
((H,)2HH0Cfl, CH,0TklPSo
2-B-C3H7HHOCR, CM2O'n1POCR
3HCM, 0CR3CH20'l'HPo-A-C,
II, HH″H2cH3cR2°’mpCH
2 Sound 3 HH En H, 0H201PCo2cH2
cH-1cH2HHOCR3C120THP Table 1p 5 R7R8 Information Eight!
7) CI HH0CH3CH2
0H133-135cO2CH3HHoCH3CH2°
H11% (decomposition) sO2°H3HHOCH, CH2°H No2II H0CH3CH20) ICo2CH (
CH3)2HH0CH3C)120HCo2C211,
HH0CH3C120HCF3HHOCH3CM2OH Br HHOCH2CM, CH20HC
H,HH0CH3CH20i! 502N(CH3)2HHoC)13CH20H(XI
:M3OH0CH3CH2°H Go2CI2CI<M2OHOCH3CH20M0CF
2CF2HHH0CR3CH20B”?R8R20X
Y 5YlCH2°C13II H0C
H3CH2°H0802CHCI2HH0CR3CH2
0HS02H5HC)I3°CH3°II2°HO80
2°H3HFi Hemp, CH20H0802C2
H, HHOCB, CH20HCO2CH2CH2
0CH, HHOCH, C1120H8O2C2H5HH
OCR, CH2011No25-CF3H0CH2CI
, 0H20H5O2″″ knee C3H73-cl ■
OCH30M20HQC,,H,5-No2HOCH
30M20H8o2N(CH3)C2H,G-No2H
0CH3C1120HC15-CI HOCH3C1
OCH3C120H5o2CHOCH3°H20H00
2°H34-F' HOCR, CH20H table 1q R7R8 emotion X X Every self! No2H)i 0CH3CH(QC2H,)2No2
HHOCH3°H2OCOCH3No2HHOCH3°
I(2SCH3 Br HHO°H3CH20'l+tlH
CH. CI II HDC113°H2OC
O2°H3F HHOCH3°H2SC
2H3F )i HOCH, °H(O
CH2CH20) So2C13HHOCH3°H2°0
″2H5So2Cm, HH0CH3CH(O
CR(CH3)CH20)So2CH,li H0
CH3CH(CCH2CH2C120)SO2(:l'
i3HH0CH2°H3°H2SCH3HHHH3CH
20°0CH3 Go20H3HH0CR3CH,, OCON(CH3)
2CO2CM, B'
H0CR3CI(OCH,, Cl2(1)Co2
0H, HHOCI, cH20°"H3"7
R8R20X
o2CB5' HCH30CI3CH28C,
H. CH3OH0CR3C1l(QC,H,)2So2N(
CH,)2HH0CH3CH20CO-1-03H70
CH3HH0CR3C12SCH. CH,,0CR3HH0CR30H20G,)CH3C
)120°H3HHOoH, CH2O°02°H3Go
, CH3CO<M2OHOCH3CH(QC2H5)2
Table 1r R7R8RII'120X - Self! No.2. HCH
3II CH3 No25<y3°H3, HOCH. CF3HCH3I C)13 Br HC2H,H0CH3CI
HCH3I CH3Cl CI
CH3I 0CR3ficH2CH3HCH3I
CH3F HC)i30H3°cn
3sO2°H3HCH3HCl 5o2CH, HC2H,)! (JCH3502
″″A-C3117HCH3I OC,y)! . co2°H, HCH, HC2115 Co2CH31(CH, Cl5CH3 0802CHCI2HCH3I 0CH3S02N
(CH3)2BcH3Hc21 (5゛ Table 18 R71555 -2- No2HHCH3C11゜No25<F, II CH30CH. CF311 HCH3CH3 Br HHCH3Cl Cl HHC)13 °2H5C1)
CI H0M30CH. 5CH2CH, HHC, H5QC, 1 (5F
HCf13CH3 father H5So2CH, H11CH,
CH3 5o2CFL5H11 back-C5H70CB. 5o27H″C3H7HIf 0M3CH3Co2
CH3I HCH3C2H5CO2°H, HC8,
CH, CH3 05020MCI2II HCM, 0CR3
! , 02N (Cf13) 2 H Summer [CM,
C.B. j Yu 55 5 LLf Rainbow 5o2N (
CH,)24-F HCH30CH30CH3II
HrC3H7CH30CF'2CF2HHll
CH30CH3CH3II HCH3CH3 Co2CH2CH, HHCH30CH. Co2Cl2Cl-OH2HII CH,CH
. CH2ocH, II HC2H50CH3So2N
(CB3)C2H,HII CH3CH30-1bH
9, HHCH3 shout) Table 2a X 5 C '204 X --ICI
HHCl, co(ocst,)2
Br HHCH3Cl(1-cH,)2F
II II OCH30M (OC1
13) 2HH, 110CH3CB(+-C113)2C
I HM CI CH (QC)! 3
). C13-CI HCH, Cl1(OC113)2CI
HII 0CR3C
H(OCH3)20CH,E HCH3Cl(t)
0M3)2CI, HH mark 1.120H,C
I (Country s+y)2Br II I
CI CH(')':'H3)2Cl,
HCii, CHC■H3)2N0211
Cfl, OCH3CM(OCH,)2GM34
-F HOCH, °H (OCH,)2C16-No2
HOCH3CH(CICI,)2'14 R
15R20X L-I Banquet No. 2) I
HCH3Cl(OCI!,)2No2H11°I
CH(田H3)2C16-F HCH2Cl, C
I(niCH,)2NO24-CI HC1l,
CB (OCH3) 2C1 Do My H country H, CMC 戊H)
)2F HHCH, °H (OCH3)2H
HHCH, C1(OCH3)2 Button, N(Cl,)2 Hhemp3CH(OCR,
)25o2N(co3)cl, HH0CR2CH,
C1(OCBI,)20CH,II C1l, C
H,co(oqa,)20So2C1l, H
HCH3C1 (OCR,)2 Table 2b “14 R15”? OX Y r
CI HHC113CH2°Chochu PBr
HHCH3°H, O'l'HPF
B 11 0G) 13C1120'fil)
'B HH0CH3CH20TklPC
13-CI HCH3CH20THPCI
HH0CH2Ck(,CH20THPOCH,HH
C1l, CH20Nk'CI, H
CH, II3 °H2°°pu2C) 13HHC1i
, °H2°3PNo2HHα; H, CI et al. 0゛stop
P CI(34-F H0CI(3CH2u'l
'1lPC16-No2H0CH3C120', l! (
PNO2I! 1ICH2CH3CH20P
R15R20X X tq day and) C1←F
HCH, C121) ChuP No24-CI HCH, 0H2UTI (PCl
5-0CH3II OCH,CH2)'r
RPF M 11 CM,
C1120THPHHHCM, Cl2O'rji
Pso2N (to cl,) 2H times 3CH20 chu PCo2N
(0M3)02B, 11 HOCH,Cl2O
'l'HPCCH3HHCH3Cl20MiP OS02su3 HHji 2 hat P table 20 R14'15 ”20AY 7CL
HII C113°H2°HBr
HHCH3Cl12°HF
HH times 3 C112011HHHIJCH,
C112°H C13°-CI HCI (3C1120HCI
II H0CR3CH20HO°H,
II HCH2Cl, CM2OHCH311H
00M3 °lI20HCH, Ti HCH3
CH20!1NO2H0M30CH, C12°H C131t-F B OCR, CH20FiC16
-No2HCCH2Cl, C120HNo2.
HHCll3CH20HC16-FMC
113CH20H JP-A-58-11647201) ! , Mu No. 24-Cl HCH, °゛(J2C1(C15-
CCH, H0CII3CH20i1F H
HCH,CI(2011H11HCH3CH20M 5o2N(CH,)2H0CH30H20H!;U2N
(CM,)C,H,HH0CR3CH20HCCH3H
HCH3Cl2011 Or, 02CH3HCM, C113CH201 (SC
2-rA-C3H7HCCH2Cl, C120H table
2d R14shi 55 yeyo”) cx HII CH
,a+(cot2cH2p)Br-,H,!
l CH3°h20C (JcH. F HHOCH3CM23C2H. H11II OCH, CCH2OC02C. C13<l H0H3CIi2SCH3CI
H to HHOCH3 (QC2H5). 0CH3HHCM, C11 (('JCH2CH2
CM20) CH3HH Country H3CH20GO-Life 103H
7CH3HH Town Cl12 (Ka2C-5No2HH0
CR3CH(CC,,)i,)2CI34-F CH
30CR3CH(OCH2C12u)C16-1402
110CR3CH20COCR3NO2H' HC
M, Cl26:,, >=2H5C16-F
HCH3CH20CU2-Q-C, R7 (+ Table 20
m, 4 y) CI H) IcR3°N+
(00H3)2Br HHC1C13CH
(OCB3)2F HH0CIr3CIi
(OCB3)2HB H0CI(3CH(OCB3
)2C13-CI HCH,C3(OCB3)2CI
HHOCH2CB3CM(OCH3)2
0CH3HHC1(3CH(OCII,)2CH3HH
0CR3CH(QC)+3)2CB3HC1C13C6
H(0°H3)2No2HHoc*3(:H(6CH,
)2C134-y Ill 0CH3C11(OC
B,)2C16-No2H0CH301+(OCII,
)2NO2HHCH2Cl(OCR,)2 C16-F HC13CM(OCC13C School
"15 R;!OX X!!, 1st
N024<l )l CH3CN, C11((
'r,ll3)2C15-OCR,I 0CI3C1
l(OCB3)2F HHCH2Cl(O
CB3)2HH11CH2Cl(OCB3)2 So,,N((:R3)2HOCR,CH(OCB3)
2■ 502N(CH3)C2) [5HI(0CR2CH30
H(QC)+3)2ocn311 HCH,cn(
oo+3)2O302CH3HHC113CH (OCI
I3)2So2-! l-C3H7HOCH,CH(OC
B,) 2 table 2f 5 to sΔ 5'' and) CI
H0M36H2CH3°li2°','HPB
rHHCH3CH20131PF
HH-0CH3CH2CTHI”HHHOCi1
3 °h20TI (■゛C13″″CI HCH
3CH201'HPCI KHQ°H2C
H3C)+20ffli)'0CH3HH0)13
°Hfl')if'CI, HHH3°H
2 (I PCI resistance, HH0M3CH2°TH
PNo2H110CH3CH20'l'klPCH,4
-F H0CH3C112°Tl1PC16-No2
HQCII3C)120THPNO2HHCH3CH2
0'rHP Cyu 6-F HC
H3CH20TH1'”14 R15R20X
X 7) No2kl HCH, CH2O
'ff1PEl 5-0CH3HOCH,
CH20TH1'''' HHCH3CH2
0'H・1'-I Hl (C136H20
'IP302N(C113)2C1i30CH3CH2
0THP■ So, NCCH3>C, 11, HH0CH30H20T
! (POC113H”26H3CI,,OIIMP0F
02CH3)I HCH3CR20THPSo2-
n-C3H7HHOCR3C120THP Table 2g X 5 555 1 -) CI B 11 CM, Cl1
2011Br' Hli OB,
CH2aBF M 11 CDl2
CB, CH20FiHHH night 3 CI (20H C1 de AH country y CH2 鑵CI H11 night 3 20HOCH3HHC
B3CH2°H CH, H110CR, CM20H CM, HH0M50M20HNO2HHO
CI(3°H20H CH,4-F 1(OCR,CH20HC16-No
2H0CH3CH20H No2HHC) i3C1120H C16-F HCM, Q (20M JP-A-1983-
116472 (33) “14”15 R20X X Colorimetric N
o24-Cl HC13CH20HC15-0CH3
H0Q(3CH20HP H11CB,
CM20MHHHCl, 0M20H 5o2N(C)C3)2HC13oCH3C120Hs
02N(CH,)C,Fl, HHOCH,CH20
HOCH3HHCH36%0k1 0502CH3HHCH2cH3C1120H, i+0
2-B-C3H7HH0CR3CH20n/ Table 2h 5 555
0)Br HHCH3CH20COCH. F HHOCH, CH25C, 11°BH
HOCII3CH2oCO2CH3C engineering 3-
CI HC113'CH25CH. CL HH0CR30H (QC2)C5)
,. OCH,H)j C1(5QM(OCR20H2CH
2U) CH3I H0CR3CH, (ACsi-C
, C7011, HHC15C1I2oCO2°2)+5
No2HH0CI301 (QC2H,)20H3JsF
H0CI(3CH(OCR2C12tJ)C16-
No2MO:II, CH20COCH. No2II CH3CH2' CH20cOC-
5C16-F HOH, CH20CO2-H-C, C
7”14 R15R20X
d) N024-010M3CH3CH2SCH3
5 憫H, H圓H, 0M2SC, 145F
HHC1I, CM(scll(CH
3) CH2S)HH)I CH3C1(QC2H5)
2so,,n(co3)2HHOCR,an(oc)I
2cii2o) So2NCCH3) (', 2H, HH0
CH30H20CONHCH30CH,HHCH,CH
20CONH7B-C, C70s02C) C3H,,H
CH3CH20COCH. 5o2-A-C3H7HHOQ(3CM(QC2H,)
2 Table 3a ”14 ”15 ”20,4 X
w, 1st ward CI HH0M3(m(OCR
,)2Br HHCH,CB(OCR,)2
r III HOCR, CH (OCR
,)2HH110OR301(OCli,)2cz
HHC1an(oC)I3)2c13-CI
HCH,CH(OCR,)2CIH)
l OCH,CI((QC) OCH,HH0H2CHI, CH(OCH3)2C
I[, HH0CH3CH(OCR,)2k
HII CI C) I(OCR,)2(m,
)I HC1l, CH(OCR,
)2No211 HOCR, C11 (OCHi),
. OH, 4-F HOCR, CI! (OCR,)2C1
6-N02HOCH,CH(OCH,)2鵡
55 animals! U Wataru N02HHC1l, C
H(OCR,)2No2HHCI Ca(ocn3
)2cz 6-r C1! , CH,C
H(OCH3)2No24<l Ii CH,0H
(OCH3)2C15-OCR,HOCH,CM(OC
R,)2F HIt CH3 to H(OC
H3)2HHHCH,CM<OCR,)2 So2N(CM,)2HOCH,OH (3)2802
! 1(OH3)C2H,HHOCH2CM, Cl1(
OCR,)2OCR,H)I CI! 30H (011
:H,)20802CI, HI(CH,CH
(OCR,). tSe 3b R14”15”; v4 X-ICI
HHC)I2CR,ctt2c+'mp
Br HHCH3CH20
THPF HH0CH3CH,, O'rH
Pit, HH0CH3CH20TII
PC13<l HCH, (H20'mPCI
HH(/C■2CH5CH20THPOCH3I
I II CH3Cl120'1MPCHHH0
CR30H20THP CH3I H (H20TklPNo2HH0 on A3
CH3CH20P Cl34-F HLlr;1130M20=PCl
6-No2H0CR3CH20'51
PNo211 II CH3CH20'ff1P
5 Notes 55 Works, Ward C16-F
M CM3C120TEPNo24-CI HC
H,CH20ffiPcl 5-OCR3
HOCH, CH20wrHCH3CH3cH20'Is
1P M 14 CB50M, CH2
61Pgo2N(cg,)2)I Hoc112c
a, ca2ochu pS resistance 2N (Cl,)C,H,HHO
CR, CH, 0'15iPOCR, 1 in 11HCH3°
20TFiP1020il, HHCH3CM
2OTl1P802-! -c, ll7H, HCICk1
3c112o'rstp button 2N (times,) CB, HH
Cl, °H2° 1O-B-C) II,
HHC1i, °1120THP table 50 Parrot 5] Eng 5♂ICI
H, Cl5CH3CH20)! Br
HHCH,CH20HF HHOCH30
M20HHHH0CR3CI20B C13-CI HCH3CM2OH Cl HH0CH3C1i20HOCH3
HHCH3Cm20H CH3HHHCl30M2kaicH3HHCH2°H3CH2oH No2HH0CH3CH20H CH34-F FI O 113 Town side C16-
H to N02HO, CH2M 2O2)I HC14, CM2OHCl
6-F II 0M30H20H”14
R15R,? OX X rNo.24
-CI HCH, C120HC1 Chaos 3H H2CH,
CH20111F I'i HCH,
ClI20H)i H■ CH3CH2
Side 802N (CI!3) 2CII3oCH3CH20H
r-02N(0M3)C2H5HHOCH3CH20H
OCR, HHCl, 0M20H 0802CH, HHCk12CH, CH20H5o27
H-C HOCR, CM2O11 Table 3d ≦ 55 animals x 2 m CI II HCH, CM (OCR, 0
M20)Br HHCH3CH20COC
H. F H11(ICI3cH2sc2)I. )I HCH,0CR30120C02C
B3C13-CI HCH30M25CH3CI
HHHCl3(m(QC,7,)2',:,l
6-F HCH3Cl20CO2-B
-C, I7 parrot 555 engineering 5ba 匝 N0
24-CI II CH3 Nisu Town c15-OCR,
HO°H3C12SC,H. F HC13(:H3eh(ocn(cH
,)aH2o)HHHCH30M(00%,)2So2N(CH3)2HHoca3cH(OCH2C1
20) SO3M(0M3)C2115HH0CH2cH
3CH20CON)ICH. OCH,HHc)I3CH20CONH"'H-C,l
l70502CH,HHCH3CH20COCH3So
2-r4-C3H7H0CH3CH(QC2H,)2!
! Table 30 555! L day and) CI
HHCH3C1(OCH3)2Br
HHCH3CH (0°H3) 2F HH0
CR3CH(OCH3)2II HH0C
H3an(oca3)2C13-CI HCH2Cl
(OCH43)2CI HH0CH2CH
3CH(OCH3)20CH3HHCH2Cl(OCH
3) 2CH3HH0CH3C1l(OCH3)2CH3
HHC13CH(OCH3)2 No2HH0CH2CH3CH(OCH3)2CH,4
-F CH30CH3CH(OCH3)2C16-N
o2H0CH3CH(OCH3)2No2HHC1(3
br H of CH(OCH3)2
C) J3CH (CICH3) 2 h x
Parked λ No24-Cl HCH, CH (OCR,)2C15
-OCR,HOCH,CM(OCH,)2FHHcH3
cH(OCH3)2 HHHc1■3cH(OCH3)2 So2N(CI(,)2HHOCH,CH(OCR3'
)2So2N(CH3)C2H5HE 0CH30H
(OCH3)2OCR3HB CH3CN, CH(
OCH3),. 08020H, HHCH30H (OCH3),. 5o2-n-C,B7HOCR,CH(OCR,)2 table
5 to R14 5] x Original 〇L HCB56H2CB3CH20THP
Br HHCH3CH20THPF
HHO°H3°H2°I'HPHI(IiOCH
,°1i20°C13-C1l CH3CH20L'MPCI
HHOCH3°H20'r'MPOCR,HH0
M3 °H2 °T1lPCM, 11
HOCH3°H2°THPCH,HH'CH,CH
20THP So2N H0CH2CH3CH20'1lff (
PCH34-F H0CR3CH20TIIPC1g
-*o2HOCH, CH20TiiPNo2HHCH,
Cl120THP ”14 R15R20X X Ox
Star! (:l 6-F HCH3cH2o
mpNO24-CI HCD3(:!H20'1ll
PCI 5″-OCH, HOCH3°H2
Kui PF 11 H0M3CH20Tk
U? HH11CD30H20'r11P SO2N(C1(3)2HC130CH3,CH20T
HPSo2N(OH,)C2H,HHOCH3°H20
THPOCH, HHCH, 0H2oTHP 0802CI3HC130H20THP5O2-...-C
3H7HocH2CH3CH20r) IP table 5g “14 R15”? OX X fCI
HH0H3CH20HBr H
HCH3CH20HF HH0CH3C1l
,,OHHHH0CH2CH,CH201i cl 3-CI HC8,CH20HCI
HHOCH, °H20HOCH3HHCH
3°H,,0H CH3HHH3°H20H CH3HHCH3CH20H No2HHOCH,CH20H CB3 4-F H
OCH3CH20HC1G-No2H0CH3CH20
H No2HH (J13C) i20H "14 R15",? OK! #
Type C16-F) ICB30H20H No2. i+-CI HCI, 0
M2(1(C15-OCR3JI 0CII3 °
H2OHF HHCIE3CH20HHH
HCH3°H20H 5o2N(CH3)2H0CR30H20HSo, N(
C)i,)C,H,HCH,OCH,CH20HoCH
,HHCH2°)! 3 0H20HOSO2CH,H)
I CH3°H20M802″″knee C5147HO
CH, 4 20H table 3h ”14 '15 R20X ヱ
-Nini CI HCH30H3CH (OCR2
CH20) Br H
HCH3CM, OC CH3F H10C
1″2°H36H2SC:2H5it
HHH3°H20°02°H3C13-CI H0H
3CH2SCH3Q HH0CH3C1i
(QC2H5). C13HHQC)13C)120CO-,4-C3H4
-C5H7CM, 0CH3CB (OCH2CH20
) C16-N02HOCH3°H20C (JCH. No2HH' CH2CH3CH20COC2H. ”14 R15R
20 people @
rCl 6-F H0M3CD20C
O2-B-c3n7No24<l HC13C125
CH3C1)OCH,H0C11,C)12SC,H3
PHHel130H(SCH(C)!3
) CiQ, S) HHHCH, CH (QC2H,)2 Gloss 2N (aH3) 20H, OCR, CHC times 20H20
)5o2N(CH,)C2H5HHO(:H3C12C
KlaiHCH. DCII3HHCH3CTl20CONH-=-C,H
70SO2CH,HHCH3Cl20°oCH3SO2
-2-C3H7H0CR3C)l(QC2H,)2 table
4a 4 C Main h A - M Co2cHHCH3Cl (QC) I3) 2C1, fl
HCH20H, CH(OCl(3)2Go20H,
HHCICl1(OCl3)2CI
II CH30CH, CH(OCR,)2HHHO
CH,0H(OCl3)2 GO2CH(CH,)25-F HCH3Cl(OC
l3)2co2ci(an,)2HCl, C1((
OCl3)2No2HHCH5Cl(OCl3)2 No26-Br HCH,CH(OCH3)2C14
-CI HCI C11(OCl3)2OF3H
H0CH3CH(OCH3)2C16-CH,CH,0
Ct13C)i(OC[13)2C,11,HHC13
CH(OCH,)20H(C1i3)2HH Town CH(
OCH3)2So2CH,HHCH,OH(00M3)
2'16 R17F1201 X
5th Ward Box 802Cl, 4-QC) 1311
0CH3CM(O訃〉)2So2CI, 6-
F HOCI(3CM(OCf!,)2302-!!
-C411,B H0H3CI((OCR,)2S
o2N(CM,)2II HCs:Ti2CH,C
H(OCR,)2S02N(C2)I5)2HHCH3
CH(00 to 3)280,,N(!0CH3)CH3I
11 (il130H(OCR,)2So2-
B-C3H7HHCH3Cl(OCl3)2sO2-4
-C3H7HH0CR30H<0CII, )2SCH3
,HH(m, CH(H3)2S(0)CI,
li H0M3+J(OCR,)2SCH2
CM, 11 HOCH, C11 (OCR
,),. 5(c)(an2), an, , II HOCH
30M<0CR3)2Table 4b Mu”1g”17 R20X Engineering
L Po Wataru cO2CH3HHCH3c) 120 chu PC
IHHCH2CH3CM2°5p CI HHO[J(3CM, 0THPHH
H(X:H3CI20'l'HP Co20H(0M3)25-F HCH3CH20T
CH3CH20THPCo2CHCM3CH20TFI
P1102HH0130M20THP No26-Br HCH3CH20THPC14-C
I HOCH3, CH20THPCF,
HH0Q(3CH20'l!HPC16-CH2O0C
R3C120THPC2115HHCH2O)t20T
)IPCH(CH,)2HCH5Cl,,0THP5o
20113H'HCH3Cl20'IP802CH34
-OCR,HOCH,(:1(20THP series)
'17 R2O: (! 7 匝5O2CH36-
F It 0CR3CH2UTklPDo2'A'
″c41f9HHCH3Cl,,0IWPSo,,N(
Cl, ), HCl, OCR,CH,0TH
PSo2N(C2H,)2HI(Chi3CH20'E
dPSo2N(OCI(3)CH, HHOil,
0H20'l5 (PSo2-H-03) 1714 1
1 °H, cH2G'IIPSo2-. 4-C, 11
7) I H0CR2CH, CH2tMj (PaCl
2)I HCH,0M20T)IPS(0)C)i
, l[HC130H20T)IPSCH2°
H,HHll3CH2Q1PS(0)-2-04H91
(H times 3CI! 20THP table 40 Mushi “17 R20/C!!!, J
Bao Co2Chi, HC113C1
12°HCI II HCH3Cl2
0HCI HCH, OCH, °H2°HI
I 11 H0CH3CH20H
Co2Cl(CH3)25-F HCH3CH20H
CO2C11(chi)2HCH2CH3CH20HNo2
HHCH3CH20H No26-Br HC113CH2oHC1k-CI
HOCH30M20HCF3HHH3CH20H C1G->30H3OCR3CH20Hcl,
n FI C113CH20HCH (CB3
)2HCH2C2H 5o2CI3HHCH3CH20)I CH3CH20)ISo2C0CII2CH3°)+2
0H Japanese Patent Application Publication No. 58-116472G9) "16 R1?) 1201 X
4So2(,”I36-F H0CR3CH2°
Hso2-B-C4H, HHCH, CM2OH3O2N
(CH,)2HHOCR,C1120Hs02N(C2
B,)2HHC)13CH20H5o2? +(OCH3
)OH3HHCM, Cl20H5o2-A-C3
)17HHCH, -0M2aHbO2 method-C3H711
II 0CH3CI (20HSCII3HHCJI2
CH3C1120H! '+(0)OH3HHC13CH
20HSC) I2OH3HH0CH3CH2011S(
0)-Me〇4H9HH0CH3Cl20H Table 4d ``亙〕2CH3 2'''A-CJ, H ri2N(CH3) SO2N<C, Ji2"16 "17"204 X
(0C) 5o2N (OCR. Shu2-- Go2CB, H0H3CH3cE1,0CO
CH,50,=a”C,)C1)l HCH2Cl
, CH(QCIL,)2So2-1-〇,)CI
HH0CR3CI23C)135CN3HI
I HOCH,CH20CONIIICR,5(0
)CH. Go, CM (CB3) 25-F HCH3CH20G
O2CH, 5CII2CH. H5(0)-Me01 cO2CM(CM, )2HcH, CH25C2H. No2HHCH3Cl(SC)120H2S)No26
-BrH, CH3CM2OC0C2H. C1I4-CI H0CR3CH (OCH2CH2C
O20)CF, HCH3(XiH3C1(
(X:H(CH3)CH2)cl 6-C
B, H0C11,C)l,,5CH3C2H,HH
CH3Cl2ocOCki. CM (0M3)2kl 0H3CH20CON(CH
,)25o2Cl, HHCH3Cl(OCt
12CH20) 沁2CM, 4daH,H"I5
°H2°0hema) 817 JouX E Yopo
匝6-F1100I3C1I, SI5 +, II OH, r:u<oc♂5)2
12HH0C1120H3C1120CO2-H-C,
I7,>2H11CH3CH20CONCCI5>2,
)CH,HHCH30H20CON(CH3)(knee〇
3H7)ly )I CH3°H2″ゝ
? 5H717)1 0CH3CH20CONH(!-C
3H7)M HCH3Cl(QC,H,)2HH0
M3CH (QC2H,)2 HHOCH3CH20C02''' total 5H7, fl,
CH30CH3CH2SCH3■ Table 40 Mouse PI3 Circulation X rCO2CM
3H)I CH3C company at3)2C1it)i
Cl2OH, Cl1(OCH3)2CI
HCH30CH3°H(t)C13)2H11H,
OCH3°H (LJCH3),. 002°H(CH,)25-F It C13°)
! (0CH3)2Co2C)l(CH,)2II C
H36H(LC)', 3)2No2H11Cl3OH(
tX:113)2No26-Br HCH3C3(of
3) 2CF3+i HOCR, Cn(OCH3)2
C16-CH, H0CH3CH ((IcR3)2C2H
,11HCl3OH(OCR,)2Cl(OH,)2H
Cl3OH(“(R3)2S02°H3HHCH,CH
(t)CH,)2SO2CH,4-OCi(,H0CH
2C13C1l(OCH3)2Hatakeθ2CI436-F
HOCH,CH(OCH,)2shi '17'?
o, (Eng. 5o2-r4-C4H9HHC13
CH(0°H3)2S(J2N(CH3)2H0CR3
C1l(OCI+3)25o2N(C2H5)2HHC
H3CH3C11(OCH3)2So2N(QC)13
) CHCl3OH(OCH3)2802-! ! -C3H
7HCH,co(iH3)2CO2-p-C3H7H0
CR2CH3Cl1(OCH3)2S”:H3CHI3
°H3CH(OCH3)2! :(+))aH3HHCH
3cn(ocH3)2E; Cl2OH, HH0CR3C
Il(OCR,)2:;(c)(Ct;2)3CH3H
noco, co(oco3)2 table 4f C
O2 di HII Cl3O) I2wa PCIH'
HCl3OH2°THP CI HH0CH30H2C'l'HPI
I HH0CH2CH3CH2 (l forceps P
CO2CH(CH3)25-F HCH3C11CH
3C1120THPCo20. HC13C
H20TIIPNo2HHCH3CH2(ITHP No2' 6-Br 11 Cl3OH
,, Oda 1'C1 Shizu CI HOCH3°H20THP
CF HCH30CR3°H2°THP> C16-CH311 Hemp 2CH3°H2° Forceps PC2H,H
HCH3°H2°T) iP cu(co3)2HHCl3OH2QT1(P!:,0
2CH3HHC13CH20'ZjlPSo2CH,l
+-OCH, H0C113CH2t)THI)”16
R17+? ;! 01 X s uniform
Kuni, C1136-F HCICH, Cl2O forceps P
So2=g-C4H9HCH3°)■2°I'HP80
21i(CH3)2M 00M3C)12Ll'l"
HP$02N(C2H5)2H':Al3C)I20"
哩5O2N (咋3) C) I3HHCl3OI (20 Lord

[
・3) 2′″!!-C3H7HCH3CH20fllP
5o2-j-C3H7110CH30H2°THpH::, Cll3HH013C120'P:, (0)C
113) I HCR20M3CH,,OTkiPm
c112CH3HH0CR3CH20'11(Ps(0
)-B-C4H9F, OCH,0I2o? I (p table
4g Mu”16 '17 R20X!
7GO20H, HCH, Cl5CI2°HCI
HHCH3CH20HCI HH
QCH3CH,OHHHH0CH3CH,,QH Go2Cl(CH3)25-F HCH2CH3CH
20HGo20H(CH3)2HC)L3CH20H1
(Shame 2HHCH3CH20H No26-Br HCH30H20HC14-CI
H 戊H3CH20H CF3HH0CH3CH,, CrH Q 6-CD5H0CH3Ch20IC2
H,HII CH30H20B 5H(C13)2H:'1i30H20H1 So2CH,11HC113C120H5o20H34
-OCH3H (eave 3CII20H"16 R
1? R20X X 7So2CH36-
F HOCH, CH201!5O2-B-C4H9H
CH,CH20H5o2N(CH,)2HOCR,CI
(20HSO3M(C2M,)2CH,CH3CH20
HSO3M(QC)B3)0M3HHCH30120H
8O2″″r4-C3H7H0M3CH20H802″
″Raw-C3H7HOCH, °H2°lISCH, II
HCH30H20H5(0)CD3HHCH30H
20H 5CH2cH, HH0CH2CH3C112C, H8(
0)-nee C4H9Hll 0CH3C1120Hmu
"Mu 4 C -178~X Eng 5th ward Ni co2°
H3HHCH2°H3682°C0CR3Cl
HHC113CH (QC2H5)2CI
HH00113°H2SCH3HHH0CH3C
)i20CON1iCH. Co2CH(CD5)25-71 HCH3CH20
CO2CH3CO2CH(CH3)2HC1130H2
SC2H. No2HHCH13C)l(OCH2CH20)No2
6-Br C13C113CH20COC2H. C14-CI II cJcH3CH (OCH2C
H2Cr12G)CF3HH0CR2CH3(':l1
(OCH(CD5)C112)C16-C13110C
H3C112SCH302H,H)I C113°l
(2°C0CH5CH(CH,)2HHC1!,
(:H20cON(CI+,)2So2CH31i
H(1:11.0H(OC112C1l,,0)
SO2di 4-OCH,H0CI(,CH2°,
C0CH. C Rx7 Emu5o20H3
6-F Country H, CH28C,? )+5So2-B-
C4H9HHCH30H(QC2H,)2So2N(C
13) 2HH0CH3C120CO2-! ! -C, H7
So2N(C21f,)2HHCH3CH20CON(
C2H5)2So2N(OCLI3)CH31(CH3
CB5CH20CON<CD3)(n-C,B7)80
2″″n″″03H7HHC13CH2°C%-0)H
2SO,,-pc3H7HH0CH3CH20CONI
I (knee〇3B?) SCH, HH0M3CH (round 15)
2 S(0)C)! 311 HCH, CM (QC, B5
)2S(0)-! ! -C4119HHOCH3CH2S
CH3 table 5° 8”16”l? R20X Y
7cO2c1131+ HcH3CH(oco
3) 2CI HHC13CH (JR3)2
cO2CH3HCH3CICH(ocII3)2CI
HHoc12CH3°H(OCR3)2H
HH0CH3CIl(QC)R3)2Go2Cl(C1
3) 25-F HCR3Cl(OCH3)2Go20
H(CH3)28 0M3CH(OCR3)2No,
HHQ12CH3CH(OCH3)2No
26-Br HCR3Cl(OCH3)2C14<l
li CI Cl1(IK';R3)2OF
3HH0CR3CH (OCH3). C16-CH5O0CH3CH (0011,)2Cno1
5HHCH3co5ccH3)2CB(CH3)2
CH20I3CH(OCH3)25o2
CH, ii li Ci(, Cl1(OCR3)
2So2CH34-OCH3H0CH3CH (OCR3
) 2shi R17R20X engineering 5baso s
o2co3g-F II 0CR3CH (OCR3
)2So27B-C4119HCR3Cl30M(OC
R3)2So, N(CR3), HIt 0CH3CH
(OCR,)2So,N(C2)I,)2! 'I
HCR3Cl(OCR3)2So2N(OCR3)CH
3Oo CM3C1ll (00I,)2+2-3-C
,H7OHC13CH(OCR,)2so2-4-c3
a7HHacm3CH(OCR3)2SCH3HHC1
3CH(OCR,)2S(Q)CH3OHCl,
CII(OCR,)2SCM2CH311110CH3
ca(')C:R3)2S(OXCH2), 口13HH
0CH3CB (time 3) 2P engineering. RA” 20 animals
X u type Wataru Go20H, HHC13C) i20
'PP,. C1, HH0H3CH20 笥P CI HHOCR3CM20? HPHHH
0CR30H20'1llP CO2CH(CH,)25-F HCl, CH
20THPGo2CH(CH3)2HCH,CH3O)
I20'ff1PNo2HHC13CH2oTHP No26-Br HCH3CH20THPC14-C
I H0CH3CH20°ff1PCF,
HH0CR3CH20111PC16-0M3H0C
H3C120fliP, HHCH3Cl2
0THPca(CH3)2HC15CH30H20TH
PSo20H3HHCM3CH2O5P So20H,4-OCR3H0CR26H,CH2°1
P”16)117 R20X
d) i02Cl, 6-F H0C
R3CH20'F)IPmi02''B-C,;H,HHC
)13CH20 RedundantP'r02NCCH3)2H0CR3
Cn20'1MP; 02N(C2H,)2HCI,
cH20TiiP1 302N(OCH3)C)H3OHCH,0H2o'I
P Enoki 2-B-C3H7HCH, C120THP; O2-
1-C3H7HHOCH3CH20TiiP3CH,H
HCH3°1120'I! )IF5(0)CH,HH0
M3CH20THP5CH2CIR3HHOcR3C)
120'I! 11P3(0)yC4B, HHOC
R3CH20THP table 50 and ``16'' 17 '20X!
rC02CM, HHCH, CH20HCI
HHC13C1 (208CI
HH0CH2CH30H20HH)t l(
QC! (,CH2°HcO2CH(CM,)25-F
HCH3°H20HC02CH(CII3)2C11
3CH3CH20HNo2HH0130M20H No26-Br HCH3CH20HC14-cl
H0CH3CHI20klCF3HH0CH3CH2
0H C16-CB31 (0CH2CH3CH20HC2H,
HCH30H3CH20H CH(CH3)2HHCH,” cH2on802CH
, HHC13C120H go20HC13C120H0CR3CB, CH series
Hachi - M Ward 5o2C136-F
H0CH3C120H8o2-H-C4H9HCH
3°H20H5o2N(CH3)2II 00M3C
H20H. 5o2N(C2H,)2HHCH3CH20H5o2N
(OCH3)CH3I HICH3(1(20H5
o2-B-C31t7. HCH3 Tsukuda 20H502-
Total C3H7H Minoh H3CM20H5CH3HHC13CH
20H 5(0)C13HHCH30M20H SCH2CH,HH0CR3CH20H5(0)-B-
C4H9HH0CR3CH20H Sheet 55
X −) C02CH3HHCH3CH2°C0CH. Q HCH3CH3C1 (QC2H,)2C
I HHOCH2°H3°H23CII3
HI(H0CH3CI20CONHCH3Co2CH(
C13) 25-F HCH3CH20GO2CI3c
O2CH(CH3)2HCH3CH2SC2H5No2
HHCH2Cl(OCR2CH20)NO26-Br
HCH3CH20':0C2)1゜C14-C1n
OCR, CH(OCH21:m2CH20)CF,
HHOCH,C11(0CH(CB3)CH2
) C16-CH3I 0CH3CH2SCH. C, H, HH, CH2Cl, CH20COCH. CB(CH3)2HHCH3CH20cIJN(Cl,
)2So2CM3HHCH3ca(aca2ah2o)
8020M34-OCR, H0CH3CH20COCH
. 5o2CH36-F H0CU3CH25C2H5-
SO2-H-C4H9HHCH2Cl (QC,, I5)
2So2N(C13)2HII 0CH3C120C
O2-B-C3H7so2N(c2u5),, H
HCH3cu2ocoN(c2It,)2so2r+(
ocn3)aH3Hu CM3CI20CON(CH
3) (B-C3H7)s02″″=-C3H7HHCM
3CI20CO″″1-C3H75O2-Raw-C3H7
Hn OCR,cn2ocosn(B-c,I7)S
CH311,OH,CH,cu(oc2)I5)2S(
0) CH3I HcH,ca(oc2n,)2S(
0)-n-04H9HHOCR30H28CH3
RA 5 animals X-Ku C02CB3HH
CH3(', II(OCH3)2CI H
HCH3°H (OCH3)2CI HH0
CR3CH(OCH3)2HHCH30CH3C1i(
OCH3). Co2CH(CH3)25-F HCH3Cl1(C
C) 13) 2co2an(aH3)2HcH, crrc
ocH3>21 No2=HCH,c=;(OCH3)2NO26
-Br HC1(3CH((X:)+3)2OF,
HHOCR,CH(01,)2C16-CH
3I 0CH3CH(Ql”l(,)2C,J,
HHCl3CH(,'C1l,)2CM(CH3
)2HH0M3CH(OCH3). 5o12CH3II II Cl5CH((,C
I(3)2So2CH34-OCH3HOCH,Cl1
(OCH,)2SO2CJI36-F H0Ci13
C4((OCR,)2L;(n2-B-C4H9HHC
H, in: H(OCH3)25'R17R20
X! m, 1 po so2++(aH3)2
HoCIr, aH(OCH3). 5o2N(c2n5)211: CH3an(oz3
)25o2N(OCH3)CH,HHCl2CH,CH
(OCH3)2S02-miC5H7HCH3CH(O
C)+3)25o2-i-C3H7IT O(m,
CH(OCH3)25CI(3HH0M3CB(OC
H3)2n(0)CH3I HCI'13 C
H(OCH3)2SCH2CH, -3 hit to HH (OC!
(3) 2S(0)(CH2)3CH3u, CH3
■H3CH (OCH3) 2 table 5f
E”16 R1?”20X
X d) ■2°H3, HCH3°h2°TH
? CI HHCH3c)I2QT)IPC
I HH0CH2CH, CH2O' HH
H0CR30H2°'IIP co2aH(aH3)25-F HC13an, om
pCo2CH(CH3)2HCH,CH20THPNo
2HHCH3CH20THP No26-Br HC113C) 120T) IPCl
4-CI H0CH3C112C Liu I
PCF3HC1l, OCH, °H20″PC16-CH
3I O Town CH20THPC2H,)i H
C13CH20n(POH(CH,)2HCH3CH2
0chuP5O2CB3HH0M3 °H,,0THP
S02CH34-OCH3II OCH3CH2
O'ff1PGo2C136-F H0C113C
1120'1VIPshi '17 R20X
X5o2-r4-C4HoH, 0H2Cl3CH2
0T%Irl5o2N(aH3)2HHOCR,co,
oTupSo2N(C2H5)2HHCH3CH20T
HPSo2N(OCH,)CH3I HCH,CH
20THP5o2-n-C, 117HCH30M2O'
l'HPSo2pi-C3H7HH0CH3CH20'
lWr'5CH3H110H3°H20°stop P S(0)CH,11HCl3CH2u” proof 5OW2°1
4. HH00M3CH20THPs (on-
n-C4H9HHOCH3Cba20'l'HP delivery-11
X ”16 R1? R,?OX Y
! , E type box 002ji HHCH3CH20
HQ HCH3CH3Cl20HCI
HH0CH3CH20HH'
OH2 to HHOCHC ■, 0H(CH3)25-F HCH3Cn2oHC
o2CH(C)I3)2HCH2Cl13C120HN
o2HHCH3OH,,0H No26-Br HCH3CH20HC1 cl
H0CH3CH20H CF3H110CH3°H2OH Cl 6-CH5O0CR3CH20HC
2H5HHCH3°H2°H CH(CH3)2HC13CH2θH 5o2CB3II HCH3CH20CH3CH2
0H3o2C, HH3°H2°H5o2C1136-F
H0CH3CH20HR16R1? R20K
! 18027B-C41t, H
HCH,C8,OH502N(CM,)2HH0CH3
C1120H802N(C,R,)2HHCM3C)I
20H802N(OCH3)CH,HHCH3Cl20
Hso2-n-C, 1t7HHC13CM20H8o2
C13C, H7H0M30CH3OH20H8cI,
8(0) CI for HHC13°H20,
HHCM3CM2OHf5cH2CH3HHOCH
3°H20H8(0)-A-C4H,HHCJCH2C
H, CH20H"16"17'20X
X d) GO2°H3HCH3°H20°
0CR3CI HHCH,CH(QC2H
5) 2CI HHOCR, CH25CH. HIiHOCH, CH2Oσbnaca. Cu2C11(CH3)25-F HCL(3CH2
0CO2CH. C02CH(CH3)2CH3CH3CH2SC2H5
No2HHCH3OH(OCR2CH20)NO26-
Br HCH3CH20COC,H. C14-C1110CH3C8 (OCR2CH2CH2
0) CF3HHoca3cH(ocH(ca3)ca2
)CH(CH3)2HC13682°C0N(CH,)
2502CH3HHCI(3CH(OCH2C■2o)
So2CH34-OCH3HOCH30M2ocOcH
.し ”17 Jou X X -I 匝5
o2CH36-F 11 0CH3CH2SC2H5
SO2-rz-C4H9HII CH30H (QCl
,I5)2So2N(CH3)2HH0CH2CH,'
:H3OC02-q-C3H7So2N(02B,)2
HH0M3an2ocoN(z2H,)2So2N(O
CR,)CH,n)T CH,an2ocoN
(an3] (B-c, o7) 1102-n-C3H7H
HCH3682°Co-4-03H7so2-4-c,
H, Hn OCH, cH2ocon (B-c, n7)
ficH,HHCH3O)I(QC2H,). 5(0)0M3HHCH3OH2(QC,,I5)2s
(o)-B-c4a9)I HOCH3°H2SC
H3 Table 6a l C R17R20X X -)Co2C
H3° HCI(30I(OCH3)2C
I HH Town CM (OCR,)2C(,
2CH31'i I (CI CH (possible 5)?C
I HHOCH,CH(OCR,)2HH
,H0CR3CH(OCH3)2 GO2CH(OH3)25-F HC03CH(OC
H3)2C02CII(CH3)2HcH3CFI(O
CH5)2No2HHC130H(OCH3)2 No26-Br HC130H(OCH3)2CF3
HHOcH2CH3CH(cIcH3)2C1g-CH
3O0CH3CH(OCH3)2C2H, HH0I,
CH(OCII,)2So2CH36-F HO
CR, CH(OCR,)21116 R1?
"20X! 7 5 o 2-B-C, 3
1, HclI, >, am<oca,)2502
N(am,), HH0CIII, cH<
+cB,)2so2i(C2H,)211 HCH
,CI((OCI(,)2So2N(OCIL,)C1
, Summer i HCM, CM (hemp) 2802-!
″c, M7Hit CH, C11 (OCR,) 280
2-510, H7II Ii times 3CH (OQi
, )25C1l, )iHcH,°)I(O
CR,”)25(0)c)C3l H0120M3
CH(OCH3)2SCH2CH3HH,0CH3CH
(OCR,)2S(0)(CR2)3C1l, HH
0CR30H (OCH3) 2 Table 6b 5 F'17 "20X X Part
Equation 2C02°)C3l 11 C1(3CM20
ffiPCI HCH3Cl3CH2p
CI HH0CH3CH20THPHHH
Oc) 12cl[3CH20THPcO,,C)f(C
H,)25-F M CM, >20TMPG
o2Cl (town) 211 Cl5CH20ffiPN
o2HRCH, CH20ffiP No26-Br HCH3Cl, mPCl
2-CI H0CR38H, 0TBPcF3H
H0CR3CH20T! P C1g-0M3H0CI(,(m20'l!PC2H5
HHCH2CH30M2O? HPCI(0M3)2HC
H,CH20THPS02°H3HHCH3cH2°'
l51PSo2CH35-OCH3H0CR3,CH2
O'JsiP R17
Y) K) 2cII, 6-F HOCH3C
m20'IK)2N(Cl,)2ft cH300
H, CI(207HPSo2N(C2H,)2H
cH, CH, Ck120TfiP802N
(OCH3)C1l, 11 it CH3C
l20THPSo2-B<, C7l H Chi
CH2O resistance PSo2-1-C3H7H H 0C
1f, CH2O bowl P8 (iH, H'
H CM3CH20TBP13(0)CI,
H H CM3C120THPSCH2
CI5H 11 0CH3CH20T! kiPS
(0)-! l-C, II, kl H 0C
kl, Ck120THP table 60 '16 R1? R;! OX
d) CO2CH,H,HCH3CH20H CI HHCH,CH30M20Hcl
HH0CH3CH20H)I
HH0CH3C120HC12″″CI Hoc
a2cH, cH2oHCF3H110CH3CH20H C16-CH,il 0CH3CH20HC2H,1
1HCM3C)120H C1l(';H3)2HC1l, CH20H5u
2CH3HHC13CH20H 802CH35-OCH,)i 0CH30120H
SO2CH36-F H0CH3CH20il”1
6 R1? R20X
802-r! -C4l, H11Cki,
CH20H802N(C1l,)2HHOCR,CH2
0H802N(C2H,)211 HCM,
c) I2o11Kuni2N (evening)) Town 11 HCM,
CH,L;kLSo2”!!-C,H7u
HCM, Qi,, OH frequency 21beh Hchi possible
Profit 20H Concave 11. II 23 countries, cm2
Information S (0) CH3I HCH, Cl2Qli5CI
I2Q1311 HOQI, C120HBCO
”)-B-04119HH times 5 mouth aOH table 6d ”16 R1? R20X
! ! , I over Co, CII, HHCM3C
H2OC0CH. CI HHCH30M(QC,H,)2CI
HHOCH, CH25CH3 HHH0CH3Q120CONHCH. Go2Cl(0M3)25-F' HCM,
CH2(6)2dico2cH(CH3)2HHC11
3CH28C2H5N02HHC:H3CH(OcH2
CH20) No26-Br H0M3CH2(XX)
C2H5C12-clHOCH30I(OCH2CI(
2CH20)CF, HH0CH3CH(O
CR(C)I,)0M2)C16-Ql, CH,O
CH, Cl2SCH. cz, HCH, 0M3an2ococn. C) I(CM,)21(0M2CH,cH2oco*(
an,)2502CI3HHCH30M(OCR2C1
20) 802CH3-)0 Town HQC, H N Tapping 2 Shigeru Shoulder
〉802CB, 6-F M OCR,C
1l, JC,) 15802B-C, H, H11Cl5C
H(QC,H,)2B02)l(OK,)2II
HOCH, CB, 0CO2-r4-C, R7802-1
-C, 1i7II H0CII, Town 0CONH
(B-C, R7) BCIK, HII CH
,CM(QC,11,)2S(0)CII,H
li CH, (m(QC,)i,)2S(0)-H-
C411, li H0QI20H, CH2S (m. Table 60 1 Shi RA 5 animals x 5 buni co2CH3
HC1(3CH3CH(OCB3)2CI
HHCH3shi0ji)2CI HHOCR3
CM(Ochi)2HHHQCH,011(OCH3)2 co2an(CH3)25-r Hca3Cl(OC
H3)2C02CH(CH3)2HCH3C1((OC
H3)2No2HHCf13CI(OCB3)2No2
6-Br HCH,CH(OCR,)2CF3'
HOCH3°H(OCH3)2C16-CM3n
ocH,co(acu,)2C2H5HHCl30H(
OCB3)20H(C113)2HHC13an(ac
u3)2So2CH,Hl(Cl30H(OCB3)2
So2CH35-OCR3HOC:H3cH((Xm,
)216 R17voX X 5a
U) SO2Cl, 6-F' H0CH3C
H(OCN43)2&02-! -C, H9)I B
C)l, CH(OCR,),. JK12N(CM,)2HH(Xm, CH(0(m
, )2So2N(C2H5)2HHCI(3CH(Oc
lN3)2802N(OCB3)CI5H0H3CH2
CH, CM(OCR,)2rl)2-M! A-C, H2
N HC1(,Cl1(OCIi,)2BO2-4
<3117HH0CH2CB30H (OCR,)280
115Hl(Q13CIR(X;H,')213(0)
CB3H0113C)I(ocIN3)260820M
, HHOCB, CH(OCR,)2S(
0)(CIlI2)30I3HHOcN43CH(OC
B3) 2 clothes 6f ”16 '17 R20X X
7) cO2CH3HHCH3cH20'l5Pcl
HH0M3CH2Q Chu PCI
HH0011,CH20THP5H
HOCH,0H20THPco2cH(cl(3)25
-r CH,'CH3Cl120TI(PCo2CH
CCH,”)2HCH,C1(,CH2O?1IPNO
2HHCH3CH20THP No26-BrII CH30H20THPC12-
CI H0CH2CH30H20THPCF3H11
0CH3CH20'm' cl 6-CH, 1100H, cR20T
1(Pc2)I5H)t CH3O(20THPCM
(C)I5), HCl, CB20THP1302
CH, HH013CH20'J1iPSo2CH35-
OCH3HOCR, CH20THP5 ~7 Import
X X d) 802C1l, 6-
F M OCR, CH2O-111PK)2-r2
-C,ll9HH0M3CH,°T! 11Pgo, *(
CI, )2a HOCR, as2onPBO-cc
ji, '12HH0M2αn 4, Kui P shame 2P (OQI
, area y HH exit 5 Tsukuda 203P button 2-C, H7HH
% °H20πPBO2-? 35 ■ 0 times
〉 Tsukuda 2°3P8CH3HHCH3c112°1P 8(0)CB, HHCM, CB213P
SCH2cjSHHOCR,CH20THPji(0)
4-04B, 11 HOCR, CB207k
lP table 6g l shi) l17 R20X X #X! c.
o2CH3HII CH3CH20HCI
HHCH3CH20HCI HH0C
H3cH20HH)I H0CH3CH20H co2CH(CH3)25-F HCH2CH30M
2OHCO2CH(CH3)2NioI3cIi20H
NO2HHC1(3CI(20H No2g-Br HCH3OH20MC12-CI
H0CR3CH20HCF, HH0CR
30H20HC16-CH3I 0CH3C120H
C2) I5HI''CH3°12°H CM(CH3)28 H(11(, C120H5o
2CH3HHCH, CH20H 5o2CH35-OCH3110CR3CH20H”1
6 R1? R20A
802CM36-F' HOCH,CH,,CJH8
02-rC41t, HC1,CCH3CH20
H802N(C,)211 HOCH3(m201
450? l1l((:2H,)2HHC113C1i
20H802N(OCH3)CH,)I HC13
cH2°H3O2-B-'C,ll7HHCII,
CH20H502 da, H7HH possible 5 Tsukuda 20H 5CH, 11HCH3CH,,0H B(0)OR3H summer (OH3Ql,,0H8CH2CH
3HHoCH2CH3c7I20H8(0)-B-C4
H9HH0CR3CH20H table 6h Shichi 5 animals X - Kowata Co2CH,
HH0M3CH20GOCB3CI HHC
H3CH(QC2H,)2C111H0CH3CH2s
CH. HHHOCH,CH20CONHCH3Co,Cl(C
H3) 25-F 11 CH3CHCH3CH20
CO2C°H(CH3)2HCH,0L2sc, a. N02HHCH3CH(0,Cll2C)+20)No
26-Br HCH3CH20COC,H. C12-CI H0CH3CH (OCFI2CB2C
H20) cr3n u 0CH3ca(ocn(
CH3) CH2) C16-OH, H0CH3CH2SC
H3C2H, +1 HC13CH20cOCH. CH(C1+3)2CH, CH3aH2occN(co
3) 25o2CH3H)t C1[3CH(OCR2
CH20) shi 8173 island
802CI, )OCR,HOCH,CH,0
COCH. 802 Town 6-F HO Ji 42”2H51
302-B-C411,H1(CH,0H(QC,II
,)2802N(CH,)2M11 0CB2CH,C
H20CO2-B-C, H7B02N(C2H,)2R
Hclly, CH20CONCCI, >2go2N(O
CR,)CM, HHC1,C1120CON(CH
3) (n-C, R7) 8°2-n-C, R7°H11>
3CH2°-1-C, R7SO2-total C, H7HH0C
R30H20COrJH(rA-C,1i7)SCH3
FI II CH3C1 (QC2)1. )28(
0) CM, H, 11CM, cH(oc
2H,)2S(0)-B-%%11Cl,
oCH, cm2scH. l RA Theory 55 1 Worker HC02CH3HCH3Cl(OCR,)24-Ca3
co2c) I, HCH, aH < times 5) 2HC0
2CH3HOCH3C11 (OCR,)2HC02C1
12C)i=cH2HC)13CI((OCR,)2H
HH0H301((OCH3)2 HSCH2Cl2CB3HOCH30 ■ SCH, l( α3 cn(■H
))2K CM(C)1332H CH2Cl3
0 (time 3) 2H CH2Cl3H CH3Cl(
OCII3) 2H F H OCH
3 an(oca3)2H CL H
0CR3aH(oca3)25-CI C1
11 Cl, C1(OCR,)2HB
r CH, 0CH3CH(OCH3)2u
N02H CH, 0H(OCH3)21(
So,N(CH3)CH2Cl, ml. CH
, (m(ocIi,)2H [,,N(0M3
)211 0011, CM(OCH,)2H
802N(OCR,)CM, H ocil,
CH(OCH,)25-F 0(OH,), C1l
, H 0CR30H(OCR,)2H
K)2CM2CH2CM, )I oCB,
CM(OCR,)211 802G'H,
H (113cH(OCH,)24-Br 80
20M, H (m, CM (OCII
,)2H Co2Cm, H CICH
(OCR,)2H No2H CI CH(
011:H,)2R17 Rls R20
X Y aH Co2Cl1,
ti Town C) I20'ff1P4-CH2Cl
2,CH3)I Cl2C1l, C3120'f
f1P1( cO2CH2CH, H OCM
, 'CM2O'mPH C02C)12CH<
B2O CH, Cl2O'1151P)I
H H CM, CH20THp
H 5CH2C12CH, H O Town C
l2O'1MPj)I SCH, )I
C) i, C; k120'151P11
CH(C13)2H OCR, Cl2O'11
C12>5H CM, Cl2O'mPH
To F ll0c >201PH
CI H 0CII, Cl2
O'1f1P) CI CI H CH
, CE20'mH Br C1
3OCR3C13OCR30 NO2OM30H,
C1120'J'HPH 502N (CH5
)CH2Cl, H CH, 0M2O'ff
1PH502N(C)13)2HOc1!3CH203
PR1? ”18 '20 X!
Shishiki Sho I 502N (OCR,) CM, H
0CH2C)l, C1(20?llPM O
CM, H CH, CH2 (MP Chaos
5 ko〉 H town ■201P5-F 0(
CIi2)3CI, H (Xi, CFI
20'151PII K)2CM2CH2CM,
H OCII3C1i20THPH Father 20M
, HCH, CH20TMP4-Br
802CR, H CH, CH,
, O'mR17R18R20X X 7H
Co2CH, HCH3CH20H143-1474-C
13CB2CH, HCl, CHQO) IIf
C02C1+20I3HOCR,OH2desiredHCo2C
112CH-cH2HC130120HHH110M3
0H20H HS>2CB,,CH,HOCR,0M20HH5CH
3HC13CB20M HCH(CH3)2HOCH3CC13CB20
CH, CI, CH3CH3CH2°HII
F H0CH2CH30H20HHC
I CH30CH30+20H)CI
CI HCH2Cl, CH2a11H
Br H0CB3%201! HN02H>
, CI! 20B B S02N(OH3)CH20M3HCH3(:
H20HH5o2N(OH,)2H0CR30H20H
R1? ”18 R20x Xd)H
802N(QCH,)CI, HOCH,0H20H
HOCH, HCH, CH20)! Chaos 505 H Town CH, 0H5-F 0(
OH2), 0M3HOCH, 0H20H11502CI
2C112CI, H0CR3C1120HH80
20M, HCH3CM2OH4-Br 8
02CM, HCH3CH20HTable 7d R17R18 information
H3Co2CH, HCH3CH20COCH. H002°H3HOCH3C12SCH. )1-Co2CH2CH=CH2HCH,CH2
0CONHCH. HHI(CH3CH20COCH3 H5CH2CH2QI3H0CH3CH2SC2H. HsCH3HcH3CH(OC112cH20)H(m
(CH3)2H0CH3CH2ocOc2H. HC82CB, HCl, CI (OCR
((m,)C120)HF HOCR,c
n(oca2an2ca2o)M CI
M OCR, 0M28CH. 5<l CI HCH, CH20COc
H. Hk CH,OCR,0M20CON(C
M,)2HN02C11NO2C113CH3C8(O
CH2c so,s(CM,)c2H,H013c
m20Cocm. R17R18R20X! One set box H802
N(C1!3)2M 0CR2C13CH,5C)1
2CH. H5o2N(03,)CL, HCM, CB(
QC,11,)2H0CII, HCH3C
l, IJX)2C155-OCR, Hemp3HCl5Q12
DCON(C,H,)2)F 0(CH2), CH3
110CR3CI420CON(C2H,),. HK)2cH,HC1,(m, (m20CO?Qi
(n-C) Table 70 X 1(CI H0CI(, CH(0(J13
)25-C1ql HC)13CH(OC
m(3)2HBr H0CH3CH(OC
H3) 2R17R18R20X! Tsujimu H80
,,N(CH3)20kl, OCR, CHCOCR,
>2M 502N (OCR,) CI, H Ql
(OCR,)2HOCH,HCH3CN, cH((X
:H, >25-OCH, OCH, HCH30H (OCf
i,)25-F o(ca2), CH3,ocH,c
g(Oc)+3)2M802CH2cH2CH3Hoc
H3CH(oc)! 3) 2H5O2cH, HCH, CI
(OCR,)24-Br5o2cfi3HC)i,
Cl1 (OCR,)2 Table 7f R17R18R20X X RiHG02CH
3HCH3CH20THP4-C13Co2°H3HC
H3CH20THPHCC2CH2CH5HOCH30
M, 0THPHC02CH2CH<H2HCH20H,
CH20THPHHHHC13C120THP H5CH2CH2C13HOCH3CH20T1iPH
SCH, kI CH3Cl120 PHC1 ((C1
(3) 2H0CR30H20THPJ (CH3CN,
HC1301120'IIPHF
H0CR2CH3C120THPHCI
H0CR301120TiiP5-CI C11
1CH3CH20THPH, Br C)1
．． OCH,CH2O'l5tP)I No2HC
H3CH2o PHf, 02N (CHO2N(CH3)
C12C113C113C'ff1PP17 ”18
Information X X m, 24 and box H80
2N(CI!3)2HOCR,CH20151Pyt
5o2ri(Oc!,)ca, hoch,
cn2owp1! OCM, HC
H3°H2cyr! 11p5421, Jiao 5H
Town CH20TklP5-F 0(OH2)3 Town H
001, CTl2O'l! IPH802CM2cH2c
H, HOQI, OH20IMPuS02cH5HC
OH20I°TIIP4-Bl-5o2cH, HC1(
3aH2asp table 7″, Yu paper '20 X X 7C (!2C
11311CH30H20H4-C13C120H3H
C113°H2°H) [002°H2°H3°H3°C
H3CH20HHco2Cha2CH″CH2HCH2O
)120H! (HHC13CD20H HεCH2C)i2CH3H0CR30H20HHSC
H3M CI(30H20H HCM(CH13)2II 0CH3C120HHC
H2Cl3HCH3°H2°H II F 11 0CM3C14
20HHCI HOCR2CM3CH20
H5-CI CI HC-C2CH,0
H20HHBr 11 0CH3CH20
HHN02HCH3CH20H H502N(CO3)CH2C113HCH3CH20
H'-1-R18R20X L m, 1st ward calm
ll502M(CH3)2HOCH3CH20HH50
2N(OCB3)CI, E 0CR3CH20H
H0Qi3IT CH3°112°H5″-0CR,
0CR3HCH3 i.e. 20H5-F 0(CH2), C
13H0CR3CH20HR&2CH2CH2CH3H
OCB, Open 20H11Fs02CH, HCH3CH
20H4-Br 5o2cn3HC13C120H table
7h “l?”18”20X
d) HCo2C)(,HCH3ca(oc2H,)2
It-CH3Co2C1l, HCH3(m2
0COCH3HCo2CH, HOCH3°H, 5CH3
HCo2C)12CI=CH2HCH3CH20CON
H.C.H. HHHCH,°H2O002CH3 H5CH2"3H2°H3H0CH3CO2SC2H. H5CH3HCH, an(oca2ca2o)HC11
(CH3)2H0CH30H20COC2H5II
CH2Cl3CH, C13CH (OCli(CH3)
CH20)n F HOCH3CI(
(00820M2C120)HCI H0
CH3CH2'yCH. 5-CI CI HCH2Cl, ,
CH20COCH3HBr HCtC,k1
2CM, OH2■ON<>,)2Hshin02HC1!3
CH(OCH2CH20)Hs, o2N(an3)c,
+t, II CH, ca2ococa. R17R18”20X X 71i 5
02N(C13>2HOCH3':H2SC'H2Q(
. H502N(OCH3)0M3HCH,CH(QC,,
H,)2M OCM, H Town 120
GO2G,,I(.chaos30C:fi3ECH3α20gloss n<cl,>2)F
, O(0M2)3CM3II QC)f3CH
20 to 0N (C2H5)2I SO2CSO2C1
12C,n OH,ca2oco(4-c,R7)I
I 5O2C113HCM30H20COtl)I
(n-C, R7) Table 8PL 8F”18 R20X X 7
HCO2CH, HCH30M(OCl3)24-CH3
Co2CH, HCH2Cl(CDd, )2HCa2OM
, H0CR30H(OC1I3)2It
CC2CH2CH-CH3I CH,OH(OCH
3) 2HHHCII2CM3CI4(OCH3)2HE
C) 12CB20H3H0CR2C13Cil (OCR
,)2H5CH311CH,' 0H(QCH,)
2n r,n(an3)2it ocH,an(
oca,)2HC1+2':83HCH30M(OCR
,)2HF HOCR,CB(OCl3)
2II CL H0CR30H (OCl
3) 25-CI CI Hca, c
o(oca,)2H3r H0CR3an(
oca,)2Hno2s CH,CH(OCH,)2
HN02H(:113)C112CM, li C
H3>(OCR,)2R17R18R20X Y
7u so2*(cu,)2HOCR,C1
(OCR,)2H802N(OCR,)0M3H0Qf
3a) I(oca,)21i 0cH3CH,CH
2Cl (OCR, ). 5p-QC,H,0CR3B, Cil, CH
(OCl,)2)FO(0M2),C1l,
I OCR,0H(OCR,)2II flat
,,CH2Cl,CB, HOCH,CB(OCR
,)2II S02CM, Hchi CH
COCR, )24-Br 80. CH, 11CH, C
M(OCi!,)2HCO2cH3HC1cH(oC1
I3) 2HN02HCI CD(OCl3)211
5o2CH,, CH2Cl, li CI
C1(OCH,)211 5020
．． HCI
CI ((ocH, N2M SCH, HCI
CH(QC:B3)2B 502-B-C,1
7H CHCOCH,>21? o-124 (minute S) □ Table 8b R17R18R20X
CH3■ C13CH,,4'ff1P4-C)l,
Co2CH, HCH, C1120'ff1PHCo2
C212CI3H0CR3cIi20THPHC02C
I2CI=CH2HCl5C1120THPHtl
HCH, 11m20THPH5CH2CH
2C13H0CII3CH20'114PHSCH,H
CH, C1120THP H011 (CIi3) 2H0CR3CH20 笥PHQl
,,CB, RC130120'I)IPH
F) 10cH3°H2O1) IPHC
I II 0c113CH2 (J3P
)CI CL HCM, CH2
011FHBr H0CH3C)120'
MPH! Parable 2 CH3
CH,0H20'1)IPHSIJ,N(CB3)riH
2CB, HCH, CH2 cheer PR1? ”18
R20X X 7--Mackerel -m-++
- B □ 502N(CB3)2II OCH3CO
CH3C112 (802N(OCR,)C1i,
HOCH3CIi, /J'NPM 00M3H
OB, CB20VP) OCl (, OCH, Hc13
c1120TEiP5-F 0CCH2)3c2I3
HOCH,0M20THPH5o2CH2C1!2C)
! 3) 10CH2CM, CB20VPMS02°M
, )t CM2C1,Q120ThP150
2°H5F, CH3CH2 employment P table 80 R1? R18R20X
HCo2CH, HCH, °H2OH 4-01, CC; 20H, II C) 120H3C1
20HHC02C02C112CCCH20M, CH
20HRCo2CH2CHsCH2HCH3Q (20H
H11u Cf13CH20H HS H2CM2C13110CR3CII20HHS
CSCH3C113CH3CH2 0C1! (':H3)2 H0CR3C
1120HHCH2Cl1. H0M3CB
,,0H)IF HOCH3 possible 20HH
':l 11 0CH3CH,,0H5
-C1', I HCH, CB,, OHHR
r fl 0CH3CH20HHN()
2 II CH3CH
20H 5 3 x x m, 1 jiang
H50PN(CM,)CM2C:B, HCl,
CF! 208BS02N(CH3)2HoCH3CH
2oHH802N (00113) CH3I OCH3
0M20HII 0013HCH3CH20H5-
OCR, OCR, HC1l, CM2O11jhF
0 (C112), CM, HOCH, 0H20
HH5o2CH2CH2CH3H0CH3CB20BH
K)2CH3HCH3CH20H 4-Br K), CH, HQl, 0H20H Cloth
8d HCo2Cl, HC1l, ca(oc
2u,,)2呵H,Co2CH,HC1! , 0M
20 (i times) HCO2 town) I OCH, CM
2SCM. HC02CI! ,,CM<M2CC1130H20CO
NHCH3HHHCCM3CH2OC02C. H! l:cH2CH2(H,H0CH2(J(3CH2
SC2H5*H5CH5HCH2CH, CM (OCR2
0H20) H0H(C113), HOCH, CH20C
OC2H. HC112CH3H0M3c)L(OCR(CH,)O
H20) HF HOCR,CH(OCH2
CH2CH,,O)H(:l H0CH3
Ck17CB35-CICI HCH3>
20CC; Cm. HBr o OCH, CH20CON (
CB,)2HNo2o OH,CH(OCR2C12
0)H502N(CB, )02H5H, CI, CB
20 COCR. H' 5o2N(C113)2H0cH3CH,! 5C
H2cH. H802N(oCII3)CH3Hc)I5cH(oc
-5) 2MOcH3CH3CH3cH20co2C2H
55-OCR,0Qi5)l C1,CH20CCN
(C,H,)25-F 0 (C12), C1l,
H0CR3CH20CONtC2+15)2M
502CB3H0H3CH20CONH (n-C, B7
) Table 80 I CIII 0CH30H(OCH3)25-
CICIH"' CB3. C11(OCH3)2H
Br HOCH3(m(OCH,>2u
No2HOH,C)ICOCR,)2R17R18R
20X
--------11802N (0M3) CH20H3
HCl12Qi3CH (OCH,). n 5o2N(aH3)2H0CR2CH,ch<
ocH,>2II 502N(OCII3)CH3
Cl, OCR, CH(OCR,)2H0CR3HCB
, C1(OCH3)2)-OCH,0CH3H0
M3CH(OCH3)2)F o(an2)3an3
HOCR,CH(OCR,)21[5o2aH2aH2
*H, H0CE3CH (OCH3) 2H father 20H3H town
q (hemp 5) 2 4-Br 5o2CI3HC113C! I(OCR,
)2 Table 8f R17R18”20X
□- HC02CH, HCH, CH2°1P 4″″CH3C02CH3HCH3CH20 PHC0
2CH2CH3HOCH3cH20 dew PHC02C12
0H, CF12HCl30H20'ff1PHHHCH
30H2°'l! HP H5CH2CH2CH3HOCH30M20THPH5
CH3H0M3CH20THP HCH(CH3)2H0CR3CH20'ff1PH0
M2CH, HCH3CH2°1P HF H0CH3CH20THPHCI
CM300H3CH20'! MP5-C1
°l HCH3>20THPHBr
H0CH20H, Cl2O'H (PHNo2H
CH2Cl, Cl2O'I%IPR17"18
R20X X 5 type!・-11 Akebonoichi
11---■----------11802N
(CH,)C820M, H2,CH2O'111P
Hs02N(CH3)2HOCH3cH20THPH5
02N(OCR,)OH,H0C1i3CH20THP
HOCH,HCH3Cl'I20'15P)00H,0
C1i, HCH, CH20THPj-F
0(CH2), CI, HOCR, Ql,,
0THPHK)2CH2CH2cII, HOCH
3 (m20fiPMS02G1'l3HCH3°H2°
3PJ+-Br 5o2cn, H01,C
H20mP table 8g R17R18R20A engineering μ stand) HCo2C
H5HCH3CH20H 4CH3CH20H4-CCH=CH2Q CE20
HH002°H2cH3HOCH2CH3cH20)!
HCo2CH2CH=CH2HCH3C20HHHHC
13CH20H H5CH2':, H2CH, HOCH30M20HH5
CII3HCH3CH20M )1 (:H(CH3)21(0CR3C120H
HC112CI3HCH30H20H HF H0CR3CH20HHCI
HOCR,0H20H5-CI CI
HCH30H1! OH+1 Br
H0CH3CH20HHN02HCH3 (m20
H R17R18R201, X a H807(OH3)CI(2OH,HCH,C120H
H502N(C)! 3) 2HOCR, 0M20HH80
2N (OCR3) CH3I OCR, CH201H times
, n CM, Report 2°H5-OCR
, OCR, HCM, CH2CM)T 0(CH
2), 0R3110CR3CB20BH502 (m2C
M2CB3CI! 30CR, CH2011HB02cH
3CH3C1I3CH20H4-Br 802CB3
HCM, C120HH table 8h 'R1? ”18 R20X
! ,；已ゆ）−■−−■――−−−−――――■■
■-m-a co2aH, HCH3CH<oC2)
I5>24-CH=CH2CH, Ill 0H30H
20COCH3HcO2cH3°H,0CH3CH2B
CH. HCo2CH5HM<H2CH,0M30H20GO)
JHCH. HHH town CH20C02CH3 H5CH2CH2cH, H0CR3CH2SCjl. HSCH, 11C130H ((K:H20H20)HC
H(0M3)2)] 0°H3CH2°00C2)I
5H0M2CH,HCH3aH(oca(ca3)ca
2o) HF H0CH3C'H (OCR2
0H2CM20)HCI HOCH2°H
3OH2SCH35-CI CI HC
H2CH, CH20COCH. HBr H0CB3>20CON(CH,
)2HNo2HCH3cH (oca2aH2o) Table 9
a
C11((XJ3C1(OCR,)25-CI C
I Cl5c′113Cl(OCR,)2HB
r)l 0CR2CH3C1K<OC
R,')2R17R18R20X!
$)H5o2N(CH,)211 0C
I13CI (OCR,7)2H5o2N, (oca3
)an, Hcycm, C1(OCH,)2M
0C1i3II CM3C1l(QC) [3)2
5-OCR, times 3 H town CH (OCR,)
25-F O (0M2), CB, H (X1m
, C11(OCH,),. HDo2CH2C142CIK3H0CH30kROC
kl,”)214 502cH3)I CH3CH
(OCR,)2HCo2di)ICIC)l((
9)B3)2HNQ211Cλ CH(OCH3)2
MK)2CM2C1120113HCI C
M(OCH3)2H502CI, LI C
I CH (OCR,) 211 帛,
M CI CM (QC) B3). Table 9b) 17 R18R20X
! ! ≦Hiki: Upper left HGo2CH, HCH
, Hit 20THP HC02CH2CB, HOoH,, CH20T
HPHCo2C);2CH=CH2HCH,0M2O'
! ! HP11 HHCH,CI,QTHP H5CH2CH2CII3HOcH3cR20THPH
SCH, HCH3CH20THP HCIl(CH3)2HOCH3CH20THPHCH
2°H3HCH, CM2O′I! MPHF
HOCR,0H20THP1i CI
H0CH2CH, CH20THP5-CI C
I HCH2CH2O) 120THPHB
r HOCH, CH20THPHNo2H
CH, CHf 笥P H#02N (0M3) CB20H, HCH, Cl201
! (P"17 R18"20X
! H802N (CH, >2HQC) in ■2o'mp
H5o2N(oca,)ca, H times, cm2a
spII 0CII3an, an, ca2o
'ritp) OCR, OCH, 11C1l, ck
120'151P5-rO(OH2), Cl5H0CR
3CH20TH? II802CH2CM2CH3HOC
H3CH20TFIPif 802C1l,
) I CH, CH2 (JTMP table 90 X R17'R18R20X
2Cl, HCl, 0H20ilII
0020M2CH3H0CR3CH2011HCo
2Cl12CHCH2HcI(,CH20HHHFi
(m, C120H H5CH2CH2CH3H0CH3CH20HHSCH
3, CH3CH3CH20H HC11(CH3)2. HCCH, CH20)
IHCH20M3HCH3cH20H HF HOCR3°H20MHCI
H0CR2CH, C120H5-CI C
I HcH2c% CC12CBr
Hoc113CH20HHNo2) [CIH
3CH20H H502N(OH3)C120HHQ(3(m,0HR
17R16”20X X 7) 11 80
, N(CI,)2H times 5 α-H802N(times)) Town
To H, CH20HII Jiao 5 b
45 Chaos) En 5 R country CH2 side 5-
IP 0 (C12), CHj ) I 0C1
1,0M20HH802CH2Cl2CH3HocH3
cCH20H118020m1311 0H3CH20i
1 table 9d '17 R18"20A X d) 111
11−++−−■−−−− +1 Co2CH, II C) 13C8 (QC2
H,)211 CA'2CH, HOCH, °ll2
SCII. HC02CH2CII<1'l2HCH3cH2oCO
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H502N(CH3)C211, HCH3Cl+20C
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m, 1 bar HC (, ; 2 cH, HCHI,
CM(OCII,)2HCo2CH5HOCH,C1
((OCR,)2HCo2CH2CH=CH2HCH,
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I HCH3O)i(OCR,)2It
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2HN02HCH 3 ports (rotating) 2 HS02N (0M3) OH20H, B CH3OH (
Tuft 3) 2R17R18” 20X X 711
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t 0M3CH(OCii,)2)OCH3,OCR
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2), CO,)1 0Qi, CH(UCH,)2I
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A X m, 2,5 units) II
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t. )TIIP table 9g X R17"18'"20X-Y 7 mo
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Co2CB3HCH2Cl (QC,H,). H002°H3°830CR, CH28CF! 3HCo
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EC2H. H5C83RCl2OM30H(OCH2CH20)H
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11 CH2CH=CH2HC13co(oca,
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0CR3C1201 (5-CI CH3I, CH
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Hase 5 55 Technique 肚用M CH2°11200H3CB, CI(,0M
2(,14H, (C)12)3CI, HC1l,
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CkifH,Z OCF3H0CR3CE20HCl Preparations Useful preparations of compounds of formula I may be prepared in a conventional manner.
. They are powders, granules, pellets, suspensions, emulsions, water
Includes Japanese preparations, concentrated emulsions, etc. Many of these things are directly
Can be applied. Spray preparations can be bulked up in a suitable medium.
, with a spray capacity of several liters to several 6 liters/ha.
I can stay. High strength composition is suitable for further compounding
Mainly used as a temporary item. Briefly, the preparation is
0.1 to 99% by weight of the active ingredient, and (a) a surfactant.
about 0.1-201a and (b) solid or liquid diluent about 1
~99.91. more specifically prepared
The product must contain these ingredients in approximately the proportions shown in Table 2.
Yes: No. 1 Oil-based suspensions, emulsions, liquids 3-50 40-95 0-15 (
(including concentrated emulsion) Aqueous suspension 10-50 40-84 1-20
Powder 1-25 7o-”s'9 o-s
0* At least one active ingredient or surfactant or diluent
= 10011111ji Of course, lower or higher amounts of active ingredients than the table may also be used depending on the intended use and
It exists depending on the physical properties of the compound. Activation of surface activity
A high proportion of
This can be accomplished by mixing in a tank or in a tank. A typical solid diluent is Watkins
“Handbook of In5ecti”
cide Dust Diluents and Ca
rriers”, 2nd edition, Doland Books Co., Ltd.
rland Books, Caldwell. N, J,)K are described, but other solids, i.e. natural and
and synthetic solids may also be used. In addition, for irrigation agents and concentrated powders,
Adsorbent diluents are preferred. Typical liquid diluents and solvents
The medium is “5olv” written by Marsden.
ents guide', 2nd edition, Interscience
Company (Inters 1ence, N, Y, ), 19
It was written in 1950. Solubility of 0.1 mo or less is concentrated
Suspensions are suitable; concentrated solutions are preferably
Stable to separation. @McCutche
on'sDetergents and I) null
sifiers Annual”, Al Arrerado Publishers
(Allurad Publ, Corp., N.J.), and Sisely and Wood.
(Wood), @] (ncyclopedia of
3urfaceActive Agen mouth”, Chemica
ChemicalPubl, Co, In
C, N, Y, ), 1964, surface activity and its
Displays recommended uses. All preparations foam
, to reduce caking, corrosion, microbial growth, etc.
may also contain amounts of additives. Methods for producing such compositions are well known. Solutions are prepared by simply mixing the components. Fine solid compositions can be produced by hammer mill or fluid energy
Manufactured by mixing in a mill and then grinding normally
It will be done. Suspension agents are manufactured by wet milling [see
U.S. Patent No. 3.0 to Litt-1er
No. 60.084]. Granules and tablets contain preformed active substances.
by spraying on shaped granular carriers or by agglomeration method.
can be manufactured. References, J.E. Browning,
“Agglomerat! on”, Chemical
Engine-ering, December 4 issue, 14
7 (1967) and Ferry, Ch.
electrical Engineer-er's Handbo
ok, 4th edition, pp. 8-59, Matsufugrow Hill Co., Ltd. (
McGrav-Hill, N. Y.), 1963. For further literature on preparation techniques, see e.g.
See: H.M. Loux, U.S. Pat. No. 123-3.
No. 61, column 6, line 16 to column 7, line 19, and Example 10 to
41°R, W, Luckenbaugh, US
National Patent No. λ309,192, Column 5, line 43 to Column 7, 6
2 rows and Example 8.12.15.39.41.52.5
3.58.132, 138-1401162-164.
166.167.169~182°H, Gys
in) and E. Knusli, U.S. Pat.
．． No. 891,855, column 3, line 66 to column 5, line 17 and execution.
Examples 1-4゜G, C, Klin-gmin
) Arrival, “WeedContral as a 8cle
nce', John Willey & Sons, Inc.
hn Wllley and Sons, Inc.
N, Y, ), 1961, pp. 81-96. J, D, -y Fryer and S, A, E
Written by Evens, @Weed Contro
l Handbook'. 5j [, Blackwell Scientific Papers
Blackwell 3cien
ti-fic Publications, Oxfo
rd), 1968, pp. 101-103. The disclosures of the above-mentioned documents are incorporated herein by reference.
It will be done. In the following examples, all parts are by weight unless otherwise noted.
It is assumed that Example 7 Irrigation agent 3-(((4-dimethoxymer-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]-2-thiophenecarboxylic acid, methyl ester SOW alkyl
Sodium lunaphthalene sulfonate 29g
Sodium ligninsulfonate 29g
Growth amorphous silica 3-gon kaori
Night ・13 regrets above
Blend the ingredients and hammer mill to remove all solids.
Qualitatively reduced to 50 microns or less, reformulated and packaged. Example 8 Wettable powder N-[(4-dimethoxymethyl-6-methylpyrimidin-2-yl)aminocarbonyl]-2-(methylsulfonyl)benzenesulfonamide 50 min alkylna
Sodium phthalenesulfonate 2 Vomit viscosity
Degree Methylcellulose 2Is Diatom±
46 Regrettably, the above ingredients are added.
rough hammer milled and then air milled.
particles, essentially all of which are less than 10 tons in diameter.
Create. The particles are reformulated and then packaged. Example 9 Granules Irrigation agent of Example 8 5. Atapa
Lugite grains 95 (US standard)
sieve 20-40 mesh;
l/-co-y (double-cone) in the blender
Spray the surface of the attapulgite particles. Dry the granules
Dry and package. 2-([(4-chloro-6-C dimethoxymethyl)pyrimidine-2 monoyl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester 25 Anhydrous crushed
sodium acid 10% crude lignin
Sulfo/acid calcium
5-tatami alkyl naphtha V sulfonic acid
Sodium 1m
Lucium/magnesium bentonite 59
Blend the ingredients, 1 mm mill, then approx.
Moisten with 129 g of water. This mixture is about 3fl in diameter.
Extrude it as a cylinder and cut it into a cylinder with a length of about 3 mm.
Produce pellets. These should be used directly after drying.
You can also grind the dried pellets to US standard
Sieve No. 20 (opening 0.84wa) Let K pass through.
I can do that. US standard sieve No. 40 (opening 0.42■)
The granules retained above are packaged for use and fines are recycled.
Can be cycled. Example 11 Oil-based suspension Trobenzenesulfonamide)' 254
Polyoxyethylene fulbitol hexao Vate 5#I high
Class aliphatic hydrocarbon oil 70% of the above ingredients
are ground together in a sand mill to obtain approximately 5 microns of solid particles.
Make it smaller than Ron. Apply the resulting thick suspension directly.
However, it is preferable to increase the volume with oil or with water.
Apply after emulsifying C+3VC. Example 12 Irrigation agent ester 20 alkyl
Sodium lunaphthalene sulfonate 4g rig
Sodium ninsulfonate 4. Low viscosity
Chillcellulose 3 attapulgiaite
69.Completely blends the above ingredients
do. Grinding in an I.mar mill to give essentially all 1
After producing particles that are 0.00 microns or smaller, the material is redistributed.
and American standard sieve No. 50 (opening 0.3 m) i
Cover with c and wrap. Example 13 Low strength granules Nylbenzoic acid, methyl ester 111°N
, N-dimethylformamide 9 Atapal
Jite particles 901 (US standard powder)
20 to 40 mesh) The above active ingredient is added to the above solvent.
Melt this solution in a double cone blender (do
Dedusted in vble coneblender)
Spray onto the particles. After the solution is sprayed, run the blender for a short time.
and then packaging the particles. Example 14 Aqueous Suspension 2-(((4-(acetyloxymethyl)'-6-methylpyrimidine methyl ester 40 wide polyamide)
Acrylic acid thickener 0.31G dodeci
Luphenol polyethyl V glycol ether 0.596
Disodium phosphate 196 Li
sodium phosphate 0.5 tips
Rivinyl alcohol 1.0 water
　　　　　　　　　　　　　　　　　　　　　　　　　
56.7 Mix the above ingredients and grind them together in a sand mill.
Crushed to essentially all particles less than 5 microns in size
Manufacture children. Example 15 Liquid formulation monoyloxymethyl)pyrimidin-2-ylcoaminocarbonyl] Rum salt 5.
951
G. Prepare a solution by directly adding the above salt to water while stirring.
and then prepared for use. Example 16 Low strength granules Nosulfonyl benzoic acid, methyl ester 0.11G a
Tapulgite granules 99.91G (rice
(Japanese standard sieve 2G-40 mesh) Dissolve the above active acid.
Dissolve this solution in a blue corn, skewer blender (double-cone blender).
Spray onto the dedusted granules in a blender. After completing the spraying of this solution, the kernel material is heated to remove the solvent.
evaporate. The material is cooled and then packaged. Example 17 Granule N-([4-methyl-6-(tetrahydropyran-2-yloxymethyl)pyrimidin-2-yl]aminocarbonyl)-2-(methylsulfonyl)benzenesulfonamide 80 Wetting agent
1. Ligninsul
Honic acid tJ [(contains 5 to 20 grams of natural sugar)
1016 attabaljiite clay
91 Blend the above ingredients and mill it to 10
Pass through a 0 mesh sieve. This material is then poured
Add to moving bed granulator to adjust air flow to gently process materials
Fluidize and apply a fine spray of water to the pressure above this fluidized material.
Spray. Continue fluidizing and spraying to obtain the desired size.
Create a range of grains. Stop spraying, but fluidization is necessary
Continue heating until the moisture is at the desired level.
It is 5 smaller than the general K11l. This material is then drained.
Take it out and sift it to the desired size range, generally 14~
100 mesh (1410 to 149 km) of material
obtained and packaged for use. Example 18 High-strength thickener (benzenesulfonamide) 991!+
Siri force knee day gel 0.54 synthesis
Amorphous silica 0.5 ref. Above components
blended and ground in a hammer mill to essentially all
passes through a US standard sieve No. 50 (0.3 m opening).
Manufacture materials for Add more of this thickener as needed.
can be matched. Example 19 Irrigation agent Luponyl)-2-(methylsulfonyl)benzenesulfonamide 9'ots dioctylus
Sodium sulfosuccinate. Rum 0.1%
Synthetic fine silica 9.9% above
The ingredients are blended and ground in a hammer mill to essentially
Particles are produced that are all less than 100 microns in size. this
The material is passed through a No. 50 K US standard sieve and then packaged. Example 20 Irrigation agent 2-chloro-N-[(4-(dimethoxymethyl)-6-methylpyriden-2-yl]aminocarbonyl]benzenesulfonamide 40m
sulfonic acid tT) A 201G Mont
Morillonite Viscous ± 401 Complete the above ingredients.
Thorough blending, rough hammer milling, then air?
rings, essentially all of which are less than 10 microns
Produce particles. This material is reformulated and then packaged
. Example 21 Oil-based additive xylene 59 above
Combine the ingredients and grind them together in a sand mill to create the essential
to produce particles that are all 5 microns or less. this
The product can be used directly, bulked up with oil, or emulsified in water.
can do. In appropriate amounts, the compounds of the present invention are powerful herbicides. They are all
Areas where complete removal of all vegetation is expected, e.g. fuel storage.
Around tanks, ammunition depots, industrial storage areas, train yards, fields.
Weeds in outside theaters, around billboards, expressways and railway areas
Wide range of usefulness for pre- and/or post-emergence control of
shows. In addition, the compound can be used in crops such as cotton, dice and
selectively eliminate weeds in wheat fields before and/or after germination.
It is also useful for extermination. The proportion of compounds of the present invention used can be selective or total deflating agents.
coexisting crop species, weed species to be exterminated,
climate and climate, the formulation chosen, the method of application, the foliage present.
It is determined by many factors, including scenery. generally speaking
Therefore, this compound is used in an amount of about 0.01~5~/ha.
Should be. In this case, light soils and/or soils with low organic matter content II
When used against K, when selectively exterminating weeds,
Or, if only short-term sustainability is required, it is necessary to
quantity is used. The compounds of the invention may be used with other commercial herbicides, such as triazines.
, triazole, uracil, urea, amide, diphenyl
Ether, carbamate and bipyridylium type herbicides
It can also be used in combination with The herbicidal properties of this compound have been demonstrated in numerous greenhouse tests.
Ru. The test method and results are as follows. Tester Digitaria sp.
(Echinochloa crusgalli), mosquito
Rasmugi (Avenifatua), Episgusa kawa
Rakemei (Cassia oftusifolim)
), Morning Glory (Ipo-moea sp, ), Onamo
Xantium sp., sorghum, corn
Kosi, daisu, rice, wheat seeds, and Cy
per'us rotundus) in the growth medium.
The chemicals are dissolved in a solvent that is harmless to the plants.
The pre-germination treatment was carried out using At the same time, three leaves
(including the leaves), the third leaflet is spreading.
Japanese bean, two-leafed crabgrass, two-leafed goldenberry,
Oats with two leaves, shrimp with three leaves (including cotyledons)
Sugusa, morning glory with four leaves (including cotyledons), four I
! (contains consonants) ona fir, four-leaf sorghum, four-leaf sorghum
Corn, two cotyledon dice, three-leaf rice, -leaf
of wheat and 3 to 5-leaf Japanese commonweed were sprayed.
. Treated and control plants were kept in the greenhouse for 16 days.
, and compared all species to controls and responses to treatments.
was visually evaluated. The evaluation method used was O, that is, no effect.
The standard was a scale from 10 to 10, ie, the maximum effect. accompany
The letter symbols have the following meanings. C = bleaching or necrosis; D = defoliation; E - inhibition of germination; G = growth retardation; H = shadowing effect; S = bleaching; U = abnormal pigmentation; Flower abscission. The evaluation of the compounds tested by this method is presented to the public.
. +□7 Table A Structure Compound 2 Compound 3 Compound 4 Table A Structure (continued) Compound 5 Compound 6 Compound 8 Table A Structure (continued) Compound 10 Compound 11 Table A Structure (continued) Compound 13 Compound 14 Compound 15 Compound 16 Table Enter Structure (continued) Compound 17 Compound 19 Compound 20 Table A Structure (continued) Compound 21 Compound 22 Table A Structure (continued) Compound 25 Compound 26 Compound 27 Compound 28゜Table A Structure (continued) Compound 29 Table entered Structure (continued) Compound 33 Compound 35 Table A Structure (continued) Compound 37 Compound 39 Table A Structure (continued) Compound 41 Compound 42 Table A Structure (continued) Compound 45 Compound 48 Takubori Taku0 c5 Country c o -■(Fl
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°C test B: Apply 1 fertilizer to 2 plastic bulb pans and add lime.
added falsington (li'allsington)
I thoroughly covered the silt loam soil. In one pan
Corn, sorghum, Kentarachy bluegrax
(Kentucky bluegrams) and several species
planted with herbaceous plants. In other pans, cotton, soybeans,
Cyperus rotundus and
I planted several types of broadleaf weeds. Herbaceous plants and broadleaf plants listed below
planted grass. Kingfisher (Digit4riasangu)
inalis), Golden millet (Echinochloac
rusgalli), oat (Avena fat)
ua), Johnson grass (Sorghum hale)
pense), greasegrass (paspalum di
latatum), Oenojtffgusa (Setar)
ia faber (order), Sparrow (: Bro
mus 5ecalinus), mustard (13ras
sica arvensis), Onamomi 0 (anth
i-am pennsylvanicum), Aobi z
(Amara-nthus retroflexus)
, Morning Glory (ipomoeah@deracea),
Cassiatora (Cassiatora)
Sida 5pinosa, velvet leaf
(Abutllon theophrasti)
, and Chilausen morning glory (1) atura str.
ammonium). Furthermore, put the prepared soil into two pots with a diameter of IZS5+.
, planted rice and wheat. Sugar is in the other 125 pots.
I planted radish. The above four containers fall within the scope of the present invention.
The seeds were pre-germinated with several test compounds. After 28 days of treatment, test subjects used the evaluation system described above.
It's easy to see how plants respond to chemical treatments with the naked eye.
evaluated. This data is shown in Table 8. at least one type
The compound is useful for pre-emergence treatment of weeds in soybean and cotton.
It can be seen that it is useful forヱ
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H1 and ζ, Drop n Test C Diameter 25.4 lined with polyethylene liner
Place the prepared phallus in two cm plastic flat pans.
'/7 toy (1'allsington) silt o -
Filled with mud. In one pan, add wheat ('['rj
ti-cum aetivum), barley (Ho
rdeumvulgare), barley (Avena)
fatua), 'Bromu
Brom s tectorum
us 5ecal 1nus), Sparrow gnome (
Alopecurus myosuroides), -
Yearling Strawberry Tsunagi Susumetsu Katapira (Poaannu)
a ), Enoj Oaawa (Setaria viri
rlis), Agropyron r.
epens), Italian ryegrass (LOI iu
m multiflorum) and Lipgutbrough
Bromus rigidus seeds were sown.
. Salsola koj (Salsola koj) in the other pan.
i), tanshi mustard (Descuraina p.
innata), Yaemugura Kinutanu (Gali
um aparine), tumble mustard (Sis
ymbrium altissium), Oukigi (
Kochia 5coparla), shepherd's purse (Caps
ellabursa pastoris), Matricaria
・Matricaria Inodora
, dogbeast (3o1anum nigrum),
Yellow Rocket (Barbarea vulgari)
a), Brassica kaber
and wild buckwheat (pol y -gonum ('o
Seeds of nvolvu [us] were sown. for a certain exam
, using rapeseed instead of wild mustard, and
Veronica pe
rsica). Pre-germination treatment of the top two pans
did. At the same time, two pans with the above plant species growing
was treated after germination. The height of the plants during treatment depends on the plant species.
The number of injuries ranged from 1 to 15. The test compound is treated with a solvent that is not toxic to plants and
I sprayed it on top of the pot. Untreated controls and solvent alone
Included for comparison. All treated plants were placed in a greenhouse for 2
Maintained for 0 days, then how many types of hardware are treated with wheat?
The present invention shows its use in the control of weeds after germination. Nioko Moth Ball □ Mouth d () Mouth. mouth. Lolo. Oo Robe 5 O N @ Mouth 10 Rorororo Rorororo 0 Rorororororo Rorororo Paper % He- ■ J: l( wo!! r-1+X ya ＼ Be Be Toru qco
1 day automa
% % cry
Mouth ~ J (4-0 Police Tomo
To 0 0 ning n se ya ＼ be K ma H so O ωtoCΦ dimension
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Test chemicals dissolved in a solvent that is not toxic to plants.
, in the overall spraying, the cords and burrows of the selected plant species.
applied to soil. One day after treatment, plants were exposed to rapid burn damage.
The wound was observed. Approximately 14 days after treatment, all
Visually compare all seeds to untreated control:)
The responses were graded. The grading system is superficial.
As mentioned above. The data are shown in Table DK. Woodstown (Woodstown)
town) in sandy loam soil and grown in a greenhouse.
Made it longer. Place the following seeds in a plastic pot (25 ts diameter)
xt x depth 1351)
: Dice, cotton, alfalfa, corn, rice
wheat, sorghum, velvet leaf (Abuti)
lon theophrasti), +x panniers (S
esbania exaltata), Ebisugusa (C
a-ssia tora), morning glory (kopomoe)
a Ip, ), Datura ('Datura
stramonium), Onamomi (Xanthiu
m pennsylvanlcum), crabgrass (Di
gitaria sp, ), Cyperus sp.
rotundus), Golden millet (Echi-noc)
hloa crusgalli)
(Se taria faberi), and
Avena fatua. next seed
Grows in the soil in a paper pot (diameter 12m x depth 13d)
Seta: sunflower, sugar beet and mustard. Everything
All plants were sprayed approximately 14 days after planting. Johnson grass, rapeseed and bindweed
This standard test was occasionally supplemented to assess abnormal selectivity. Several compounds tested using this procedure were
and post-emergence suppression of weeds in soybean. C.J.
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Continuation of page 1 QInt, C1,3 identification code Office serial number //
(C07D 409/12
-239100 7431-4
C333100) 8214-4
C317100) 7432-4
C (C07D 405104
-239100 7431-4
C317100) 7432-
4C (C07D 405104
-239100 7431-
4 C319100) 8214
-4C (C07D 405/12
-251100 7132
-4 C309100) 716
9-4C priority claim October 20, 1982 ■ United States
(US) C434038 8

Claims (1)

[Claims] 1. In the formula, X is CH, OCH, CI, C, H, t or QC, H. , 2 is CH or N, Y is CH, OR, CH, SRCH(ORs)*, OC
H,OR,,0CR(OCHm)COtRs or R is F(,C(0)R3,Co,R,,C(t)NRsR
eRl is C, -C, alkyl, R1 is -CH, CH, -, -CH(CHl)CHI- or -CH, CB, CH! -, R is C, -C, alkyl, R4 is C1-C, alkyl, R1 is H or OH, R1 is Cs Cm alkyl, Q is O or S , Human is R7 H, C, -C, alkyl, ClC4 alkoxy,
F, CI, Br, No, ,OF, ,CO,R
,,SO,NR1゜R□,5OtN(OCHs)CHO8O! R15(0)nRts, LCF ILCHF
t, LCF, CF, H%C, -C, alkenyloxy or c, -c, alkyl (OCR, or OC,
H. R1 is H, F, CI, Br, CF3, NO2,
CI -C, alkyl or C, C, alkoxy, Ro is C1-C4 alkyl, CH, CH! OCH CH
, CH, CI or CH, CH=C11, Ashi, R1
° and 81% are independent KC1-C, alkyl, R4 is C,-C4 alkyl, CH, CH, OCH,,C
HICHI CHloCHm t or C, -C4 alkyl (substituted with 1 to 3 atoms of F%elf or Br), R3, is C, -04 alkyl or CHt CH=CH
t], n is 0 or company 2, L is O, S or SO2, R34 is lid:) [, 'CH,, OCH,, F, CI
, B r , NOI , 80t NR to Rs
s 1080t Rt * or S (0)n Rt
s, Ro is H, CI, Br%CH, OCR, or No. and R6, is L c, -c, alkyl, Cl-C4 alkoxy, F% C1% Br%CFs % Cod%m, S
o.NRI. B-1 801N (OCf(s) CHs or S (0) nRs s, Rtv) i, F, CI, Br, CHB or OC
H. , W is O or S, and W is 0 or S, R8, is HlCt 4 alkyl, C, -c, alkoxy, F, CI, Br, No, , Co, R @, 80, NR
,. R11, So, N(OCH,)CH, or S (
0' ) n Rt s desi 1 R1, 7i ("1, No, CF coin・, So
,N(OCR,)CB,,80*NRts R11,0
80*Rt*, 5(0)nRu or c, -C, alkoxy (substituted with 1 to 5 atoms of CB or F), and R7° is H or CH; However, 1) Rs. and the total number of carbon atoms in R11 is 4 or less, (when 21x is elf, 2 is C, H"t'ase, (
3) When W is O, R3, is) l, CI, Br. CH, or CHsRs, (4) W is O and R8, is H, CI, Bri
or CHs, the person is strong, (51 When Wl is S, R1° is H and Hiroso (61
Y is 0CR1OR, or 0CR(OCf(,)COl
When Rl, 2 is CH, and a chemically suitable salt thereof. Z Wl is O, X is CHst7t is OCH. and R3° is H. A compound according to claim 2, wherein R3° is H. 4, A is R1 is C, -Cs alkyl, C, -C, alkoxy, C
I, Not, Cow Re, So, (CI-〇, 7
A/kill), 80. NR1°R81, So! N(0C
Fis ) CH I080, R,,, C Tori OC Torimakuha L
C^B, R14 is CB,, OCR,, Cl, 0
80. CH, or SOs <C1-C, alkyl)
Adashi, R1@a CHs, OCR,, Cl, SO
sCM, or S ()*A/ (CHa)w,
R1, is CM, , CI, By, O@R,i or 80. C.E. The compound according to claim 3 JA.翫 The compound according to claim 1, claim 4, wherein A is. 2. The compound according to claim 1, which is formed by 3-(L(4-dimethoxymethyl-6-methylpyriden-2-yl)-aminocarbonylcoainosulfonyl)-2-thiophenecar 1M7eL methyl ester. 7.2-Chloro-N-[(4-dimethoxymethyl-6-
2. The compound according to claim 1, wherein the compound is methylpyryzyn-2-yl)adenocalf-nyl]penzenesulfonyl. The compound according to claim 1, which is &2-(((4-dimethoxymethyl-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester. 9,N-[( The compound according to claim 1, which is 4-dimethoxymethyl-6-methylpyrimidin-2-yl)aminocarbonyl-2-methylsulfonylbenzenesulfonamide.10,N-((4-dimethoxymethyl- 6-methylfurimicin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamitoal, the compound according to claim 1. 11, 2-[[:(4-dimethoxymethyl-6- methylpyrimidin-2-yl)aminocarbonyl]minosulfonyl]benzoic acid, 2-7'royl ester,
A compound according to claim 11. IL2-[([4-methyl-6-(tetrahytotetrapyran-2-yloxymethyl)pyrimi,-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, described in claim 1 The compound according to claim 1, which is xa 2-([[4-(hydroxymethyl)-6-methylpyrimidin-2-yl]aminocarbonyl]aminesulfonyl]benzoic acid, methyl ester. 14 2-1: ([4-(acetyloxymethyl)-6
-Methylpyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methylpyrimidin-2-yl]methyzyl-5-ester; 15.9 Scope of Xu Xindong An effective amount of the compound described in paragraph 1;
A composition suitable for controlling undesirable plant growth, characterized in that it consists of at least one surfactant, a solid or liquid inert diluent. 16. An effective amount of the compound according to claim 2,
A composition suitable for controlling undesirable plant growth, characterized in that it consists of at least one surfactant, a solid or liquid inert diluent. 17. An effective amount of the compound according to claim 3,
A composition suitable for controlling undesirable plant growth, characterized in that it consists of at least one surfactant, a solid or liquid inert diluent. 1 & an effective amount of the compound according to claim 4;
and at least one surfactant, a solid or liquid inert diluent, and 19.4. A method for suppressing undesirable plant growth characterized by comprising an effective amount of the compound according to item 5 and at least one of a surfactant and a solid or liquid inert diluent. composition suitable for. 2. Suppressing undesirable plant growth, characterized by comprising an effective amount of the compound according to claim 6 and at least one of a surfactant and a solid or liquid inert diluent. composition suitable for. 2. A method for inhibiting undesirable plant growth characterized by comprising an effective amount of the compound according to claim 7 and at least ill of a surfactant and a solid or liquid inert diluent. composition suitable for. 22. an effective amount of the compound according to claim 8;
A composition suitable for controlling undesirable plant growth, characterized in that it consists of at least one surfactant, a solid or liquid inert diluent. 2. An effective amount of the compound according to claim 9 and at least one of a surfactant and a solid or liquid inert diluent to inhibit undesirable plant growth characterized by dryness. composition suitable for 2. Effective bone of the compound according to claim 10,
A composition suitable for controlling undesirable plant growth, characterized in that it consists of at least one surfactant, a solid or liquid inert diluent. 2. an effective amount of the compound according to claim 11;
A composition suitable for controlling undesirable plant growth, characterized in that it consists of at least one surfactant, a solid or liquid inert diluent. 2. an effective amount of the compound according to claim 12;
A composition suitable for inhibiting undesirable plant growth, characterized in that it consists of a surfactant, a solid or liquid inert diluent, and 411 species. 2. An effective amount of the compound described in claim 13;
A composition suitable for controlling undesirable plant growth, characterized in that it consists of at least one surfactant, a solid or liquid inert diluent. 2. Suppression of undesirable plant growth, characterized by comprising an effective amount of the compound according to claim 14, section 6, and at least one of a surfactant and a solid or liquid inert diluent. composition suitable for 2. A method for suppressing the growth of undesirable plants, which comprises applying an effective amount of the compound according to claim 1 to the area to be protected. 3α A method for suppressing the growth of undesirable plants, which comprises applying an effective amount of the compound according to claim 2 to the area to be protected. 31. A method for suppressing the growth of undesirable plants, which comprises applying an effective amount of the compound according to claim 3 to the area to be protected. 32. A method for inhibiting the growth of desirable dark plants, which comprises applying an effective amount of the compound according to claim 4 to the area to be protected. 3& A method for suppressing the growth of undesirable plants, which comprises applying an effective amount of the compound according to claim 5 to the area to be protected. 34. A method for suppressing the growth of undesirable plants, which comprises applying an effective amount of the compound according to item 6 to the area to be protected. 3& A method for suppressing the growth of undesirable plants, which comprises applying an effective amount of the compound according to claim 7 to the area to be protected. 36. A method for suppressing the growth of undesirable plants, which comprises applying an effective amount of the compound according to claim 8 to the area to be protected. 37. A method for suppressing the growth of undesirable plants, which comprises applying an effective amount of the compound according to claim 9 to the area to be protected. 3& A method for inhibiting undesirable plant growth, which comprises applying an effective amount of the compound according to claim 10 to the area to be protected. 39. A method for suppressing the growth of undesirable plants, which comprises applying an effective amount of the compound according to claim 11 to the area to be protected. 40. A method for inhibiting undesirable plant growth, which comprises applying an effective amount of the compound according to claim 12 to the area to be protected. 41. A method for suppressing the growth of undesirable plants, which comprises applying an effective amount of the compound according to claim 13 to the area to be protected. 4z A method for inhibiting the growth of undesirable plants, characterized in that an effective amount of the compound according to claim 14 is applied to the area to be protected. 43, where X is CH3,0CH8, CIXC! H, or QC,H
. , 2 is CH or N, Y is CH20R, CH*SRs, CH(ORt)t
,0CEl t OR1,0CH(OCH,)Co,R
, or R1 is -CH2CHt-1CH(CH@)C
H*- or -CHt CHt CHt-adeshi, R8
is cl-C, alkyl, R1 is C1-C, alkyl, R1 is H or CH, R6 is C,-C, alkyl, QtiO or S, A is R9 R1 is H%C, -C, alkyl, C, -C, alkoxy, F% CI, Brz No@, CFs, CO
*R*, So, NR,. RSS,so,N(ocH,)
CH,,OS Ot Rt 1.5(0)nRts-L
CFs, LCHFt, LCF, CF, H, Cm-c,
Alkenyloxy or C,, -C,alkyl (OCR
, or QC,H,), and R1 is [(% F, 01% Br, CF,, No,
,C,-C. Alkyl or C, -C, alkoxy, Ro is C
1-C4 alkyl, CH, CH! OCH CH, CH,
CI or CH, CH=CH, and R1° and R
11 is independent K C, -C, alkyl, R1, RC, -C, alkyl, CHt CElm QC
Hz, CH2CH1CH10CHs or C,-C,alkyl()', substituted with 1 to 3 atoms of ci or Br), and Rls is Cl-04alkyl or CHtCH=CH
z, n is 0 or 2, L is 0, S or SO, R14 is Hh CH3,0CHI, F, CI,
Br, NO,,80*NRte Rsii08OtR+
t or 5(0)nR11, RII is H, CI, Br%CH,, OCH, t or NO
. And R1 sound is H, C, -C, alkyl, C, -C, Ak:
i $ CI, F, CI, Br%CF1, Go, R,
,□SO,NR,. Rtt, SO*N(OCHs)
CHs or 5(0)nR, , Ro is H%F%CI, Br, CH, or OCR. , W is 0 or S, and W is O'' or S, and Ro is H%Cl-4 alkyl, C,-C4 alkoxy, F, CI, Br%No, %C (Mis, 5OINR
1°R,,,80,N(OCH,)OH, or 5(0
). R1, R1, ke C1, No@, CFm, CO*R@, 80
,N(OCH,)CH,,5O2NR1°R11,O2
0,R11,5(0)HRts or CI-C, alkoxy (substituted with 1 to 5 atoms of CI or F), and R1° is H or CH, with α) R3 The total number of carbon atoms in ゜ and R11 must be 4 or less, (2) When X C1 is present, 2 is ctt"t', (3) When W is O, R4 is H, CI , Br. CH,t or Co, R, is, (4) When W is O and Rla is )T, CI, Br or CH, then one is and (6) Y is OCH!0R1t or 0CH(OCH,)C
o, Rj, 2 is CH. In preparing the compound of general formula I, X, R1° and 2 are υ as defined above, and CH((&Q), A compound of the general formula Ago, NσW1, where R, R, and R3 are as defined above, is reacted with a compound of the general formula Ago, NσW1, where A and Wl are as defined above to obtain the general 44. A process according to claim 43, characterized in that the reaction is carried out in an inert aprotic solvent at a temperature ranging from 0° C. to reflux. 45. 21b where A% 46, Formula 1c, ld and 1e (IC) (Id) In preparing the compound of formula 1c, ld and 1e (IC) (Id), where A compound of 1b is contacted with at least one equivalent of an alkyl carboxylic anhydride, carbonyl chloride, chloroformate carbonyl chloride or alkyl isocyanate in an inert solvent in the presence of an excess of acid acceptor at a temperature from 0°C to reflux. 47, W, is O, R7° is H, and X is CH, or OCR, the patent Yokobuki's 4&R*
etfHfashi, and Xti, CHst or OCH,
46. The method according to claim 45. 49. The method of claim 47, wherein Y is CHI(ORs)*. 50, A is R1 C1-03 alkyl, C, -C, full: l',
C1, Nov, C0tRo, 5Ox (CI Cs
Full Kill), SO! NRI(IRIii5OtN(OCH)
s) CHs, O8O*Rt CH, OCH, or LC
FIH, R14 is CHOCH, CI, 080. CH, or So, (C, -C, alkyl), R1゜ is CH0CHs, CI, SOlCHm or SO*N
(CHs) *, and R1, is CHI, CI,
Br, COIR@ or 80, CH, The method according to claim 48 or 49. The method described in Paragraph 50 of the same. 5z3-[”[(4-dimethoxymethyl-6-methylpyrimidin-2-yl)-aminocarbonyl]aminosulfol)-2-thiophenecarboxylic acid, methyl ester, the method according to claim 43. 53, 2-chloro-N-[:(4-dimethoxymethyl-
6-methylpyrimidin-2-yl)aminocarbonyl]
Claim 43, which is benzenesulfonamide
The method described in section. 44. The method according to claim 43, wherein 2-CCC4-dimethoxymethy/I/-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester. 55, N-((4-dimethoxymethyl-6-methylpyrimidin-2-yl)aminocarbonyl]-2-methylsulfonylbenzenesulfonamide. 56, N-( (4-dimethoxymethyl-6-methylpyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide-1'al, Claim 4
The method described in Section 3. 57. The method according to claim 43, wherein 2-(((4-dimethoxymethyl-6-methylpyrimidin-2-yl)aminocarbonyl]annosulfonyl]benzoic acid, 2-propyl ester. 5&2- 44. The method of claim 43, wherein ((4-methyl-6-(tetrahydropyran-2-yloxymethyl)pyrimin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester. 59, 2-C[:[:4-(hydroxymethyl)-6
-Methylpyrimidin-2-yl]aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester, claims ppr, 47. The method described in section. 60 2-(([4-(acetyloxymethyl)-6-
Methylpyrimidin-2-yl]aminocarbonyl]aminosulfonyl]Andiro Kojo, methyl ester, the method according to claim 43.